Prosecution Insights
Last updated: April 19, 2026
Application No. 18/149,300

PROCESS FOR PRODUCING (R)-3-HYDROXYBUTYL (R)-3-HYDROXYBUTYRATE

Final Rejection §103§112§DP
Filed
Jan 03, 2023
Examiner
STEADMAN, DAVID J
Art Unit
1656
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Government Of The Usa AS Represented By The Secretary Department Of Health
OA Round
2 (Final)
58%
Grant Probability
Moderate
3-4
OA Rounds
3y 1m
To Grant
87%
With Interview

Examiner Intelligence

Grants 58% of resolved cases
58%
Career Allow Rate
553 granted / 955 resolved
-2.1% vs TC avg
Strong +29% interview lift
Without
With
+29.1%
Interview Lift
resolved cases with interview
Typical timeline
3y 1m
Avg Prosecution
50 currently pending
Career history
1005
Total Applications
across all art units

Statute-Specific Performance

§101
9.0%
-31.0% vs TC avg
§103
26.7%
-13.3% vs TC avg
§102
19.4%
-20.6% vs TC avg
§112
29.6%
-10.4% vs TC avg
Black line = Tech Center average estimate • Based on career data from 955 resolved cases

Office Action

§103 §112 §DP
DETAILED CORRESPONDENCE Status of the Application The present application is being examined under the pre-AIA first to invent provisions. Claims 1-9 are pending in the application. Applicant’s amendment to the claims, filed August 25, 2025, is acknowledged. This listing of the claims replaces all previous versions and listings of the claims. Applicant’s remarks filed August 25, 2025 in response to the non-final rejection mailed April 24, 2025 are acknowledged and have been fully considered. The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action. Claim Objections The objection to claim 1 is withdrawn in view of the amendment to claim 1 to recite “(R)-3-hydroxybutyl-(R)-3-hydroxybutanoate” in lines 11-12 and to add a conjunction between steps (ii) and (iii). In the interest of clarity, it is noted that the term “(R)-3-hydroxybutyl (R)-3-hydroxybutyrate” in lines 1-2 of claim 1 is the same compound as “(R)-3-hydroxybutyl-(R)-3-hydroxybutanoate” in lines 11-12 of claim 1. The objection to claims 2-9 is withdrawn in view of the amendment to claims 2-9 to replace “A” with “The.” The objection to claim 3 is withdrawn in view of the amendment to claim 3 to recite “wherein the alcohol is ethanol.” The objection to claim 9 is withdrawn in view of the amendment to claim 9 to add a conjunction between “sodium borohydride” and “nickel borohydride.” Claim Rejections - 35 USC § 112, Second Paragraph The rejection of claim 9 under 35 U.S.C. 112 (pre-AIA ), second paragraph, is withdrawn in view of the amendment to claim 9 to replace “reducing agent” with “hydride transfer reagent.” Claim Rejections - 35 USC § 103 The rejection of claims 1-5, 8, and 9 under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Clarke et al. (WO 2010/021766 A1; cited on the IDS filed on May 16, 2023; hereafter “Clarke”) in view of O’Neill et al. (Tetrahedron Asymmetry 5:117-118, 1994; cited on the IDS filed on May 16, 2023; hereafter “O’Neill”) and Zhong et al. (U.S. 2005/0182235 A1; cited on the IDS filed on May 16, 2023; hereafter “Zhong”), the rejection of claim 6 under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Clarke in view of O’Neill and Zhong as applied to claims 1-5, 8, and 9 above, and further in view of Seebach et al. (Organic Syntheses Collective 9:48, 1998; 71:39, 1993; cited on the IDS filed on May 16, 2023; hereafter “Seebach”), and the rejection of claim 7 under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Clarke in view of O’Neill, Zhong, and Seebach as applied to claims 1-6, 8, and 9 above, and further in view of Casey et al. (“Advanced Practical Organic Chemistry,” Blackie, London, 1990, pp. 158-160; cited on the IDS filed on May 16, 2023; hereafter “Casey”) are withdrawn in view of the amendment to claim 1, part (iii) to recite “wherein the transesterification is carried out between 1 and 20 hours.” Clarke teaches a transesterification reaction between ethyl (3R)-hydroxybutyrate and (R)-1,3-butanediol in the presence of a lipase enzyme (paragraph bridging pp. 4-5 and Example 1 at p. 12), the reaction typically being conducted for a period of about 96 hours (p. 5, top). The combination of Clarke, O’Neill, and Zhong does not teach or suggest transesterification between ethyl (3R)-hydroxybutyrate and (R)-1,3-butanediol carried out between 1 and 20 hours. Claims 1-5, 8, and 9 are rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Clarke in view of Linko et al. (JAOCS 72:1293-1299, 1995; cited on the IDS filed May 16, 2023; hereafter “Linko”), Zhong, and O’Neill. This rejection is necessitated by the amendment to claim 1. As amended, the claims are drawn to a process for the production of (R)-3-hydroxybutyl (R)-3-hydroxybutyrate comprising: contacting poly-(R)-3-hydroxybutyrate with an alcohol to transesterify the poly-(R)-3-hydroxybutyrate under transesterification conditions to produce an ester of (R)-3-hydroxybutyrate and the alcohol, wherein the transesterification is carried out between 1 hour and 30 hours; separating the product of step i) into a first and second portion and reducing the first portion of the (R) 3-hydroxybutyrate ester in a solvent and an organic or inorganic reducing agent to form (R)-1,3-butanediol; and contacting under transesterification conditions the (R)-1,3-butanediol from step ii) with the second portion of the transesterified ester of (R) 3-hydroxybutyrate to produce (R)-3-hydroxybutyl-(R)-3-hydroxybutanoate, wherein the transesterification is carried out between 1 and 20 hours. Regarding claim 1 step (iii), Clarke teaches a method for the synthesis of (3R)-hydroxybutyl (3R)-hydroxybutyrate (i.e., (R)-3-hydroxybutyl (R)-3-hydroxybutyrate or (R)-3-hydroxybutyl-(R)-3-hydroxybutanoate) by a transesterification reaction between ethyl (3R)-hydroxybutyrate and (R)-1,3-butanediol in the presence of a lipase enzyme (paragraph bridging pp. 4-5 and Example 1 at p. 12). Clarke teaches the reaction is typically conducted for a period of about 96 hours (p. 5, top). The differences between Clark and claim 1 are: Clarke does not teach the lipase-catalyzed transesterification reaction is carried out between 1 and 20 hours as recited in claim 1, part (iii), and Clarke does not teach producing the ethyl (3R)-hydroxybutyrate and (R)-1,3-butanediol reactants according to steps (i) and (ii) of claim 1. Regarding carrying out a lipase-catalyzed transesterification reaction between 1 and 20 hours, Linko teaches optimizing reaction conditions for lipase-catalyzed transesterification by screening different lipases and varying molar ratios of reactants, amount of water, temperature, and time (p. 1293, Abstract). Linko teaches the progress of lipase-catalyzed transesterification reactions conducted for up to 5 hours (p. 1294, column 1, bottom), up to 7 hours (p. 1296, FIG. 2; p. 1297, FIG. 4; p. 1298, FIG. 7), up to 10 hours (p. 1298, FIG. 6), and up to 5 hours (p. 1298, FIG. 8), which are within the range of “between 1 and 20 hours” in claim 1, part (iii). In view of Clarke and Linko, it would have been obvious to one of ordinary skill in the art to modify Clarke to conduct the lipase-catalyzed transesterification reaction between 1 hour and 20 hours. According to MPEP 2144.05.II.A, where the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation. In this case, the general conditions of claim 1, part (iii) are disclosed by Clarke with the exception that Clarke teaches transesterification for 96 hours while claim 1, part (iii) recites “between 1 and 20 hours.” According to MPEP 2144.05.II.B, the presence of a known result-effective variable would be motivation for a person of ordinary skill in the art to experiment to reach another workable process. In view of Linko, one of ordinary skill would have recognized that the time course for a lipase-catalyzed transesterification reaction is a result-effective variable and given that the time for conducting a lipase-catalyzed transesterification is a result-effective variable, one would have been motivated to experiment to discover the optimum or workable ranges for the lipase-catalyzed transesterification reaction of Clarke. One would have expected success to modify Clarke to conduct the lipase-catalyzed transesterification reaction between 1 hour and 20 hours because, in view of Linko, it would have required no more than routine experimentation to modify Clarke to conduct the lipase-catalyzed transesterification reaction between 1 hour and 20 hours. Regarding producing ethyl (3R)-hydroxybutyrate according to step (i) of claim 1, Zhong teaches preparing an alkanoic ester by combining a polyhydroxyalkanoate (PHA) ester with a protic catalyst and a monohydric alcohol (paragraph [0044]) with the PHA ester being exemplified by poly-3-hydroxybutyrate (PHB) and the alkanoic ester being exemplified by methyl- or ethyl-3-hydroxybutyrate (paragraph [0065]). Zhong teaches the protic catalyst is exemplified by various acids (paragraph [0060]). Zhong teaches the PHA can be chiral PHA (paragraph [0108]), specifically the D-isomer (paragraph [0109]), which is the same as the R-isomer. Example 1 of Zhong (p. 9, paragraph [0126]) describes a process for preparing ethyl (3)-hydroxybutyrate from PHA (polyhydroxybutyrate) and ethanol. Zhong teaches a reaction time of 2 hours and 4 hours, noting that after 2 hours, the percent yield of ethyl-3-hydroxybutyrate from PHA was 77.8% and after 4 hours, the percent yield was 92%. Reaction times of 2 hours and 4 hours as taught by Zhong are within the range of “between 1 hour and 30 hours” in claim 1, part (i). In view of Clarke and Zhong, it would have been obvious to one of ordinary skill in the art at the time of the invention to prepare the ethyl (3R)-hydroxybutyrate reactant of Clarke according to Zhong. One would have been motivated and would have expected success because the method of Clarke requires ethyl (3R)-hydroxybutyrate as a reactant and Zhong taught a routine method for preparing ethyl (3R)-hydroxybutyrate. Regarding producing (R)-1,3-butanediol according to step (ii) of claim 1, O’Neill teaches reducing ethyl-(R)-3-hydroxybutyrate with lithium aluminum hydride in ethyl ether gave (R)-1,3-butanediol (p. 117, bottom). Ethyl ether is a solvent and lithium aluminum hydride is an inorganic reducing agent. In view of Clarke and O’Neill, it would have been obvious to one of ordinary skill in the art at the time of the invention to prepare the (R)-1,3-butanediol reactant of Clarke according to O’Neill. One would have been motivated and would have expected success to do so because the method of Clarke requires (R)-1,3-butanediol and O’Neill taught a routine method for preparing (R)-1,3-butanediol. Regarding separating the product of step i) into a first and second portion according to step (ii) of claim 1, Clarke’s method requires ethyl (3R)-hydroxybutyrate and (R)-1,3-butanediol and in order to produce the ethyl (3R)-hydroxybutyrate and (R)-1,3-butanediol reactants, one of ordinary skill in the art would have recognized two alternatives. One alternative is the independent production of two separate batches of ethyl-(R)-3-hydroxybutyrate, one batch for the ethyl (3R)-hydroxybutyrate of Clarke’s method and the other batch for production of (R)-1,3-butanediol of Clarke’s method. The second alternative is producing a single batch of ethyl-(R)-3-hydroxybutyrate and using a portion of the single batch of ethyl-(R)-3-hydroxybutyrate for the synthesis of (R)-1,3-butanediol. At the time of the invention, one would have been motivated to practice the second alternative for a more efficient production of the ethyl-(R)-3-hydroxybutyrate and the (R)-1,3-butanediol required for Clarke’s method. One would have expected success because it would have required no more than routine experimentation to separate ethyl-(R)-3-hydroxybutyrate produced according to Zhong into first and second portions. Regarding claim 2, the recitation of “the poly-(R)-3-hydroxybutyrate is obtained from corn starch or sugar cane” is interpreted as a product-by-process limitation embedded into the claimed method. Given that product-by-process claims are not limited to the manipulations of the recited steps, only the structure implied by the steps, the poly-(R)-3-hydroxybutyrate taught by Zhong is considered to be encompassed by claim 2. Regarding claim 3, Zhong teaches ethanol for producing the ester with ethyl (3)-hydroxybutyrate. Regarding claim 4, Zhong teaches the ratio of alcohol to PHA is about 1, 2, 4, 6, or 10 moles to 1 mole (paragraph [0054]). Regarding claim 5, the ester production process of Zhong is carried out with a protic catalyst (paragraph [0044]) being exemplified by various acids (paragraph [0060]). As such, one of ordinary skill in the art at the time of the invention would have recognized that the process of Zhong is carried out in acidic conditions. Regarding claims 8 and 9, O’Neill teaches lithium aluminum hydride to convert ethyl-(R)-3-hydroxybutyrate to (R)-1,3-butanediol (p. 117, bottom). Therefore, claims 1-5, 8, and 9 would have been obvious to one of ordinary skill in the art at the time of the invention. Claim 6 is rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Clarke in view of Linko, Zhong, and O’Neill as applied to claims 1-5, 8, and 9 above, and further in view of Seebach. Claim 6 is drawn to the process according to claim 1 wherein the product of step i) is treated to neutralise the acid, remove the alcohol by distillation. The relevant teachings of Clarke, Linko, Zhong, and O’Neill as applied to claims 1-5, 8, and 9 are set forth above. The combination of Clarke, Zhong, and O’Neill does not teach neutralizing the acid and removing the alcohol by distillation following synthesis of the ester as recited in claim 6. Seebach teaches synthesis of methyl-(R)-3-hydroxybutyrate by combining poly-(R)-3-hydroxybutyrate with concentrated sulfuric acid in methanol (first page, middle). Seebach teaches (in relevant part) that following the reaction, saturated sodium bicarbonate is added and the crude product is distilled under reduced pressure to give pure methyl-(R)-3-hydroxybutyrate (bp 61-62/18 mm) (first page, middle). In view of the additional teachings of Seebach, it would have been obvious to one of ordinary skill in the art at the time of the invention to neutralize the acid used for the synthesis of ethyl-(R)-3-hydroxybutyrate with saturated sodium bicarbonate and to purify the product by distillation. One of ordinary skill in the art would have been motivated to do so because of the teachings of Seebach, which resulted in a purified ester, the ester being identical to or nearly identical to the ester produced by Zhong. One would have expected success because the ester of Seebach is identical to or nearly identical to the ester produced by Zhong and because of the routine experimental methodology provided by Seebach, which resulted in a purified ester product. Therefore, claim 6 would have been obvious to one of ordinary skill in the art at the time of the invention. Claim 7 is rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Clarke in view of Linko, Zhong, O’Neill, and Seebach as applied to claims 1-6, 8, and 9 above, and further in view of Casey. Claim 7 is drawn to the process according to claim 6 wherein the distillation is carried out at a temperature of 110° C to 150° C. The relevant teachings of Clarke, Linko, O’Neill, Zhong, and Seebach as applied to claims 1-6, 8, and 9 are set forth above. The combination of Clarke, Linko, Zhong, O’Neill, and Seebach does not teach distillation carried out at a temperature of 110 oC to 150 oC as recited in claim 7. Figure 9.10 of Casey shows that distillation at a reduced pressure of about bp 61- 62/18 mm is equivalent to distillation at about 150 oC at atmospheric pressure (Figure 9.10, page 159). In view of the additional teachings of Casey, it would have been obvious to one of ordinary skill in the art at the time of the invention to purify the ethyl-(R)-3-hydroxybutyrate product by distillation at 150 oC. One of ordinary skill in the art would have been motivated and would have had a reasonable expectation of success to do so because Seebach taught purification of an ester that is identical to or nearly identical to the ester produced by Zhong by distillation at bp 61-62/18 mm and Casey shows that distillation at a reduced pressure of about bp 61- 62/18 mm is equivalent to distillation at about 150 oC at atmospheric pressure. Therefore, claim 7 would have been obvious to one of ordinary skill in the art at the time of the invention. RESPONSE TO REMARKS: In summary, applicant argues the combination of Clarke, O’Neill, and Zhong fails to teach or suggest the following limitations: (1) the source of the butanediol and, specifically, that the butanediol must be derived from the same source as the hydroxybutyrate; (2) that the butanediol is obtained by reduction in a solvent using an inorganic or organic reducing agent; (3) that the butanediol is derived from polyhydroxybutyrate; (4) that the hydroxybutyrate is derived from polyhydroxybutyrate in a reaction carried out over 1 to 30 hours; and (5) that a second transesterification step is performed and carried out over 1 to 20 hours; the rejection relies on impermissible hindsight reasoning; and neither Seebach nor Casey remedy the alleged deficiencies of Clarke, O’Neill, and Zhong. Applicant’s arguments are not found persuasive. Regarding applicant’s argument that the combination of Clarke, O’Neill, and Zhong fails to teach or suggest all claim limitations, contrary to applicant’s arguments, for the reasons set forth above, the combination of Clarke, O’Neill, and Zhong teaches or suggests all limitations of claims 1-5, 8, and 9, including the applicant’s noted limitations (1)-(5). Regarding applicant’s argument that the rejection relies on impermissible hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See MPEP 2145.X.A. In this case, the rejection relies only on knowledge which was within the level of ordinary skill at the time the claimed invention was made and not on applicant’s disclosure. As stated above, Zhong teaches a routine method for producing the ethyl (3R)-hydroxybutyrate reactant of Clarke and O’Neill teaches a routine method for producing the (R)-1,3-butanediol reactant of Clarke and one would have been motivated to produce ethyl (3R)-hydroxybutyrate and (R)-1,3-butanediol according to the methods taught by Zhong and O’Neill in order to obtain the reactants needed to practice the method of Clarke. Regarding applicant’s argument that neither Seebach nor Casey remedy the alleged deficiencies of Clarke, O’Neill, and Zhong, given that the combination of Clarke, O’Neill, and Zhong teaches or suggests all limitations of claims 1-5, 8, and 9, and provides sufficient motivation and expectation of success to arrive at the invention of claims 1-5, 8, and 9, the rejection based on the combination of Clarke, O’Neill, and Zhong is not deficient. For these reasons, it is the examiner’s position that the claimed invention would have been prima facie obvious to one of ordinary skill in the art at the time of the invention. Claim Rejections - Double Patenting The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969). A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b). The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp. The rejection of claims 1-7 on the ground of nonstatutory double patenting as being unpatentable over claims 1-7 of U.S. Patent No. 11,566,268 (cited on Form PTO-892 mailed April 24, 2025) is withdrawn in view of the amendment to claim 1 to recite “reducing…in a solvent and an organic or inorganic reducing agent to form (R)-1,3-butanediol” because claim 1 of the patent recites “reducing the first portion in a solvent using a ketoreductase or an alcohol dehydrogenase to form (R)-1,3-butanediol.” Claims 1-9 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-7 of U.S. Patent No. 11,566,268 in view of O’Neill. Although the claims at issue are not identical, they are not patentably distinct from each other. This rejection was previously applied only to claims 8 and 9 and has been modified to include claims 1-7, which is necessitated by the amendment to claim 1. Regarding claim 1 of this application, claim 1 of the patent recites a process for the production of (R)-3-hydroxybutyl-(R)-3-hydroxybutyrate from a single starting material feedstock of poly-(R)-3-hydroxybutyrate, comprising: (i) contacting the poly-(R)-3-hydroxybutyrate with an alcohol to transesterify the poly-(R)-3-hydroxybutyrate under transesterification conditions to produce an ester of (R)-3-hydroxybutyrate and the alcohol, wherein the transesterification is carried out between 1 hour and 30 hours; (ii) separating the product of step i) into a first and second portion and reducing the first portion in a solvent using a ketoreductase or an alcohol dehydrogenase to form (R)-1,3-butanediol; and (iii) contacting under enzyme-catalyzed transesterification conditions the (R)-1,3-butanediol from step ii) with the second portion of the transesterified ester to produce (R)-3-hydroxybutyl-(R)-hydroxybutanoate, wherein the enzyme-catalyzed transesterification is carried out between 1 hour and 20 hours. Claim 1 of the patent does not recite “reducing…in a solvent and an organic or inorganic reducing agent to form (R)-1,3-butanediol” as recited in claim 1, part (ii) of this application. O’Neill teaches producing (R)-1,3-butanediol by reducing ethyl-(R)-3-hydroxybutyrate with lithium aluminum hydride. In view of O’Neill, it would have been obvious to one of ordinary skill in the art at the time of the invention to modify the method of the claims of the patent to produce (R)-1,3-butanediol by reducing the ester with lithium aluminum hydride. One would have been motivated and would have had a reasonable expectation of success to do so because, while the claims of the patent recite an enzymatic reduction of the ester, O’Neill teaches an alternative, routine method for producing (R)-1,3-butanediol by reducing ethyl-(R)-3-hydroxybutyrate with lithium aluminum hydride. Regarding claim 2 of this application, claim 2 of the patent recites the process according to claim 1, wherein the poly-(R)-3-hydroxybutyrate is obtained from corn starch or sugar cane. Regarding claim 3 of this application, claim 3 of the patent recites the process according to claim 1, wherein the poly-(R)-3-hydroxybutyrate is transesterified in step (i) using ethanol. Regarding claim 4 of this application, claim 4 of the patent recites the process according to claim 1, wherein the weight ratio of alcohol to poly-(R)-3-hydroxybutyrate is from 1:1 to 10:1. Regarding claim 5 of this application, claim 5 of the patent recites the process according to claim 1, wherein the step (i) is carried out in acidic conditions. Regarding claim 6 of this application, claim 6 of the patent recites the process according to claim 1 wherein the product of step (i) is treated to neutralize the acid and remove the alcohol by distillation. Regarding claim 7 of this application, claim 7 of the patent recites the process according to claim 6 wherein the distillation is carried out at a temperature of 110° C to 150° C. Regarding claims 8 and 9, O’Neill teaches lithium aluminum hydride to convert ethyl-(R)-3-hydroxybutyrate to (R)-1,3-butanediol (p. 117, bottom). Therefore, claims 1-9 of this application are unpatentable over claims 1-7 of the patent in view of O’Neill. RESPONSE TO REMARKS: Applicant requests the rejections be held in abeyance until the claims are deemed allowable, at which time Applicant will file a terminal disclaimer. Applicant’s remarks are acknowledged. Conclusion Status of the claims: Claims 1-9 are pending in the application. Claims 1-9 are rejected. No claim is in condition for allowance. Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a). A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action. Any inquiry concerning this communication or earlier communications from the examiner should be directed to DAVID J STEADMAN whose telephone number is (571)272-0942. The examiner can normally be reached Monday to Friday, 7:30 AM to 4:00 PM. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, MANJUNATH N. RAO can be reached on 571-272-0939. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /David Steadman/Primary Examiner, Art Unit 1656
Read full office action

Prosecution Timeline

Jan 03, 2023
Application Filed
Apr 21, 2025
Non-Final Rejection — §103, §112, §DP
Aug 25, 2025
Response Filed
Oct 15, 2025
Final Rejection — §103, §112, §DP (current)

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Prosecution Projections

3-4
Expected OA Rounds
58%
Grant Probability
87%
With Interview (+29.1%)
3y 1m
Median Time to Grant
Moderate
PTA Risk
Based on 955 resolved cases by this examiner. Grant probability derived from career allow rate.

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