Invention Grant
- Patent Title: Synthesis process for chiral cyclopropyl ethynyl tertiary alcohol compound
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Application No.: US15551142Application Date: 2015-10-23
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Publication No.: US10214480B2Publication Date: 2019-02-26
- Inventor: Nan Zhao , Fei Jiang
- Applicant: Shanghai Desano Pharmaceutical Co., Ltd. , Yancheng Desano Pharmaceutical Co., Ltd. , Jiangsu Puxin Pharmaceutical Co., Ltd.
- Applicant Address: CN Shanghai CN Jiangsu CN Jiangsu
- Assignee: Shanghai Desano Pharmaceutical Co., Ltd.,Yancheng Desano Pharmaceutical Co., Ltd.,Jiangsu Puxin Pharmaceutical Co., Ltd.
- Current Assignee: Shanghai Desano Pharmaceutical Co., Ltd.,Yancheng Desano Pharmaceutical Co., Ltd.,Jiangsu Puxin Pharmaceutical Co., Ltd.
- Current Assignee Address: CN Shanghai CN Jiangsu CN Jiangsu
- Agency: Millen White Zelano and Branigan, PC
- Agent Csaba Henter
- Priority: CN201510083083 20150215; CN201510316165 20150610
- International Application: PCT/CN2015/092754 WO 20151023
- International Announcement: WO2016/127661 WO 20160818
- Main IPC: C07C213/10
- IPC: C07C213/10 ; C07C213/00 ; C07C215/70 ; C07D265/18 ; C07B53/00

Abstract:
Provided is a synthesis process for a chiral cyclopropyl ethynyl tertiary alcohol compound, where a chiral amino alcohol or a chiral amino diol is reacted in the presence of an alkaline reagent and a salt to obtain an optically active propynyl alcohol compound. In particular, the process includes (1) reacting cyclopropyl acetylene with a chiral inducing agent, a chiral auxiliary reagent and zinc halide in an organic solvent in the presence of an alkaline reagent and a sulfonate or a sulphinate to obtain a first reaction mixture; (2) reacting the resultant first reaction mixture with 5-chloro-2-aminotrifluorobenzophenone to form (S)-2-amino-5-chloro-α-cyclopropyl acetylene-α-trifluoromethylbenzyl alcohol. The process avoids an organic zinc reagent and a Grignard reagent, and has the advantages of safe production, an environmentally friendly route, low production costs, a high resultant product yield, a high chiral ee value and is suitable for industrial production.
Public/Granted literature
- US20180029975A1 SYNTHESIS PROCESS FOR CHIRAL CYCLOPROPYL ETHYNYL TERTIARY ALCOHOL COMPOUND Public/Granted day:2018-02-01
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