Synthesis method of chiral (S)-nicotine
US11981653B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Apr 11, 2022 |
| Grant date | May 14, 2024 |
| Priority date | — |
| Expiry date | Dec 29, 2042 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D401/04
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
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.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.