Title:
METHOD FOR PREPARING S-NICOTINE
Document Type and Number:
WIPO Patent Application WO/2023/284057
Kind Code:
A1
Abstract:
A method for preparing S-nicotine. A nicotinic acid ester and γ-butyrolactone are used as starting materials, and are successively condensed under the action of an alkaline catalyst; a reflux reaction with concentrated hydrochloric acid is carried out to achieve ring opening to obtain 4-chloro-1-(3-pyridine)-1-butanone; a reaction with an amination reagent is carried out under an alkaline condition to obtain 4-amino-1-(3-pyridine)-1-butanone; chiral hydroxyl is produced under the induction of (+)-B-Chlorodiisopinocampheylborane to obtain (S)-4-amino-1-(pyridin-3-yl)butan-1-ol; then chlorination is carried out; ring closing is carried out under the action of an alkali to obtain S-nornicotine; finally, amine methylation is carried out to obtain S-nicotine. The reaction conditions are mild and easy to implement, S-nicotine having a single configuration can be obtained with high selectivity, S-nicotine has a high yield and high purity, the steps are simple, the starting materials are low in cost, and the method is particularly suitable for industrial S-nicotine production.
Inventors:
ZOU JUN (CN)
ZOU YANG (CN)
LIU MEISEN (CN)
LUO WEIXIAN (CN)
ZOU YANG (CN)
LIU MEISEN (CN)
LUO WEIXIAN (CN)
Application Number:
PCT/CN2021/112793
Publication Date:
January 19, 2023
Filing Date:
August 16, 2021
Export Citation:
Assignee:
SHENZHEN ZINWI BIO TECH CO LTD (CN)
International Classes:
C07D401/04
Foreign References:
| CN110256403A | 2019-09-20 | |||
| CN111004212A | 2020-04-14 | |||
| CN104341390A | 2015-02-11 | |||
| CN110357853A | 2019-10-22 | |||
| CN112409329A | 2021-02-26 | |||
| US20180030028A1 | 2018-02-01 | |||
| US5045550A | 1991-09-03 | |||
| CN104341390A | 2015-02-11 | |||
| CN1233829A | 1999-11-03 |
Other References:
CAS , no. 614-18-6
See also references of EP 4140992A4
See also references of EP 4140992A4
Attorney, Agent or Firm:
BEIJING WEIZHENG PATENT AGENCY CO., LTD. (CN)
Download PDF: