Title:
INTERMEDIATE OF PREGABALIN AND PREPARATION METHOD THEREFOR
Document Type and Number:
WIPO Patent Application WO/2022/083728
Kind Code:
A1
Abstract:
Disclosed are an intermediate of pregabalin and a preparation method therefor. Provided are a compound as represented by formula (I) and a preparation method therefor. The preparation method for the compound as represented by formula (I) is any one of the following methods: method (1), comprising the following steps: reacting a compound as represented by formula (III) with nitromethane in an organic solvent in the presence of a base, and obtaining the compound as represented by formula (I) by means of chiral separation; and method (2), comprising the following steps: reacting the compound as represented by formula (III) with nitromethane in an organic solvent in the presence of a base under the action of a catalyst as represented by formula (II). The methods have moderate reaction conditions and low-toxicity, simple and readily available raw materials, are easy to operate, are easily used for production in a large scale, and can be used for synthesizing pregablin.
Inventors:
LI JIANQI (CN)
WANG GUAN (CN)
HE CHASHENG (CN)
ZHAI ZIRAN (CN)
ZHOU YANG (CN)
DU XINLI (CN)
WANG GUAN (CN)
HE CHASHENG (CN)
ZHAI ZIRAN (CN)
ZHOU YANG (CN)
DU XINLI (CN)
Application Number:
PCT/CN2021/125648
Publication Date:
April 28, 2022
Filing Date:
October 22, 2021
Export Citation:
Assignee:
SHANGHAI INST PHARMACEUTICAL IND (CN)
CHINA STATE INST PHARM IND (CN)
CHINA STATE INST PHARM IND (CN)
International Classes:
C07D263/26; C07C205/51
Foreign References:
| US20120029230A1 | 2012-02-02 | |||
| US20100010219A1 | 2010-01-14 | |||
| CN109942446A | 2019-06-28 |
Other References:
HE CHASHENG, ZHAI ZIRAN, ZHOU YANG, LI JIANQI, WANG GUAN: "A new synthetic route for the preparation of pregabalin", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS INC., US, US , pages 1 - 7, XP055923832, ISSN: 0039-7911, DOI: 10.1080/00397911.2021.1919710
TOVAR-GUDINO ERIKA, MORALES-NAVA ROSMARBEL, FERNANDEZ-ZERTUCHE MARIO: "Diasteroselective conjugate addition of diethylaluminum cyanide to a conjugated N-enoyl system: an alternative synthesis of", CANADIAN JOURNAL OF CHEMISTRY, vol. 92, no. 1, 1 January 2014 (2014-01-01), CA , pages 45, XP009535945, ISSN: 0008-4042, DOI: 10.1139/cjc-2013-0397
PALOMO CLAUDIO, OIARBIDE MIKEL, LASO ANTONIO, LÓPEZ ROSA: "Catalytic Enantioselective Aza-Henry Reaction with Broad Substrate Scope", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 127, no. 50, 1 December 2005 (2005-12-01), pages 17622 - 17623, XP055923835, ISSN: 0002-7863, DOI: 10.1021/ja056594t
LELE WEN, LIANG YIN, QILONG SHEN, LONG LU: "Enantioselective Organocatalytic Michael Addition of Nitroalkanes and Other Nucleophiles to β-Trifluoromethylated Acrylamides", ACS CATALYSIS, AMERICAN CHEMICAL SOCIETY, US, vol. 3, no. 4, 5 April 2013 (2013-04-05), US , pages 502 - 506, XP055437906, ISSN: 2155-5435, DOI: 10.1021/cs300806w
COLONNA STEFANO, RE ALBERTO, HANS WYNBERG: "Asymmetric Induction in the Michael Reaction by Means of Chiral Phase-transfer Catalysts derived f tom Cinchona and Ephedra Alkaloids", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, 1 January 1981 (1981-01-01), pages 547 - 552, XP055923836, DOI: 10.1039/P19810000547
TOVAR-GUDINO ERIKA, MORALES-NAVA ROSMARBEL, FERNANDEZ-ZERTUCHE MARIO: "Diasteroselective conjugate addition of diethylaluminum cyanide to a conjugated N-enoyl system: an alternative synthesis of", CANADIAN JOURNAL OF CHEMISTRY, vol. 92, no. 1, 1 January 2014 (2014-01-01), CA , pages 45, XP009535945, ISSN: 0008-4042, DOI: 10.1139/cjc-2013-0397
PALOMO CLAUDIO, OIARBIDE MIKEL, LASO ANTONIO, LÓPEZ ROSA: "Catalytic Enantioselective Aza-Henry Reaction with Broad Substrate Scope", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 127, no. 50, 1 December 2005 (2005-12-01), pages 17622 - 17623, XP055923835, ISSN: 0002-7863, DOI: 10.1021/ja056594t
LELE WEN, LIANG YIN, QILONG SHEN, LONG LU: "Enantioselective Organocatalytic Michael Addition of Nitroalkanes and Other Nucleophiles to β-Trifluoromethylated Acrylamides", ACS CATALYSIS, AMERICAN CHEMICAL SOCIETY, US, vol. 3, no. 4, 5 April 2013 (2013-04-05), US , pages 502 - 506, XP055437906, ISSN: 2155-5435, DOI: 10.1021/cs300806w
COLONNA STEFANO, RE ALBERTO, HANS WYNBERG: "Asymmetric Induction in the Michael Reaction by Means of Chiral Phase-transfer Catalysts derived f tom Cinchona and Ephedra Alkaloids", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, 1 January 1981 (1981-01-01), pages 547 - 552, XP055923836, DOI: 10.1039/P19810000547
Attorney, Agent or Firm:
SHANGHAI BESHINING LAW OFFICE (CN)
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