- Patent Title: Kinetic resolution reaction of a (1RS,2SR)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound, a process for preparing optically active trans-α-necrodyl isobutyrate, and a process for preparing optically active γ-necrodyl isobutyrate
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Application No.: US17580874Application Date: 2022-01-21
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Publication No.: US11746078B2Publication Date: 2023-09-05
- Inventor: Tomohiro Watanabe , Takeshi Kinsho , Takeru Watanabe , Miyoshi Yamashita , Yusuke Nagae
- Applicant: Shin-Etsu Chemical Co., Ltd.
- Applicant Address: JP Tokyo
- Assignee: Shin-Etsu Chemical Co., Ltd.
- Current Assignee: Shin-Etsu Chemical Co., Ltd.
- Current Assignee Address: JP Tokyo
- Agency: Myers Bigel, P.A.
- Priority: JP 21010360 2021.01.26
- Main IPC: C07C67/08
- IPC: C07C67/08

Abstract:
The present invention relates to a process for preparing a (1S,2R)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (S,R)-(2), wherein R1 represents a monovalent hydrocarbon group having 1 to 6 carbon atoms, and a bold wedged bond represents the absolute configuration, and a (1R,2S)-(2-acetoxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (R,S)-(3), wherein R1 is as defined above, a hashed wedged bond represents the absolute configuration, and Ac represents an acetyl group, the process comprising: subjecting a (1RS,2SR)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (RS,SR)-(2), wherein R1 is as defined above, and a hashed unwedged bond represents a relative configuration, to a kinetic resolution reaction with a lipase in the presence of vinyl acetate to obtain the (1S,2R)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound ((S,R)-(2)) and the (1R,2S)-(2-acetoxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound ((R,S)-(3)).
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