Method for synthesizing (S)-nicotine and intermediate thereof
US11884644B1 · kind B1 · utility
Assignee
Inventors
Key dates
| Filing date | Sep 1, 2023 |
| Grant date | Jan 30, 2024 |
| Priority date | — |
| Expiry date | Sep 1, 2043 |
Classification
- Technology area (CPC Y)Emerging Cross-Sectional Technologies
- CPC primaryY02P20/55
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Disclosed is a method for synthesizing (S)-nicotine and an intermediate thereof, which belongs to the field of synthesizing a heterocyclic compound. A chiral amino group is introduced into 4-hydroxy-1-(3-pyridyl)-1-butanone by transaminase chiral catalysis in the presence of an amino donor to obtain (S)-4-amino-4-(3-pyridyl)-1-butanol. An N-methylation reaction is performed on (S)-4-amino-4-(3-pyridyl)-1-butanol with a methylating agent to obtain (S)-4-(methylamino)-4-(3-pyridyl)-1-butanol. The intermediate is reacted with an acylating agent or a halogenating agent to convert an alcoholic hydroxyl group into a sulfonate group or a halogen. Finally, a ring closure reaction is performed to obtain (S)-nicotine in an alkaline condition. The raw materials are cheap and readily available, the reaction conditions are mild, the operation is simple, and the cost is low. A single configuration of (S)-nicotine can be obtained with high selectivity, and thus the method is particularly suitable for industrial production of (S)-nicotine.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.