Invention Grant
- Patent Title: Synthesis method of chiral (S)-nicotine
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Application No.: US17718313Application Date: 2022-04-11
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Publication No.: US11981653B2Publication Date: 2024-05-14
- Inventor: Jun Zou , Yang Zou , Meisen Liu , Weixian Luo
- Applicant: SHENZHEN ZINWI BIO-TECH CO., LTD
- Applicant Address: CN Guangdong
- Assignee: SHENZHEN ZINWI BIO-TECH CO., LTD
- Current Assignee: SHENZHEN ZINWI BIO-TECH CO., LTD
- Current Assignee Address: CN Shenzhen
- Priority: CN 2110781163.8 2021.07.10 CN 2111029637.X 2021.09.03
- Main IPC: C07D401/04
- IPC: C07D401/04

Abstract:
The present application discloses a synthesis method of chiral nicotine from nicotinate and γ-butyrolactone, including the following steps: Step S1: performing condensation under an alkaline condition, and performing ring opening reaction with hydrochloric acid; Step S2: reacting with (+)—B-diisopinocampheyl chloroborane to produce a chiral hydroxyl group; Step S3: performing a chlorination reaction; and Step S4: performing cyclization under an alkaline condition to obtain the chiral nicotine. In the present application, nicotinate and γ-butyrolactone, both cheap and readily available, are used as raw materials, so as to reduce the production cost of (S)-nicotine. (+)—B-diisopinocampheyl chloroborane is used to reduce a carbonyl group of an intermediate to obtain a target chiral center. The (+)—B-diisopinocampheyl chloroborane induces the production of a chiral hydroxyl group, chlorination and cyclization are performed to form chiral (S)-demethylnicotine, and finally amine methylation is performed to obtain (S)-nicotine with photochemical activity.
Public/Granted literature
- US20230044688A1 SYNTHESIS METHOD OF CHIRAL (S)-NICOTINE Public/Granted day:2023-02-09
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