Title:
METHOD FOR PREPARING CHIRAL SYNTHETIC NICOTINE
Document Type and Number:
WIPO Patent Application WO/2023/284058
Kind Code:
A1
Abstract:
A method for preparing chiral synthetic nicotine, comprising the following steps: S1, performing a condensation reaction on nicotinate and γ-Butyrolactone under the action of an alkaline condensate to obtain a first mixture; S2, adding an acidic substance to the first mixture to perform a ring-opening reaction to obtain a second mixture; S3, separating 4-chloro-1-(3-pyridine)-1-butanone from the second mixture, and reacting same with chiral tert-butylsulfinamide to obtain chiral N-(4-chloro-1-(pyridin-3-yl) butene)-2-methylpropane-2-sulfinamide; S4, first reacting chiral N-(4-chloro-1-(pyridin-3-yl) butene)-2-methylpropane-2-sulfenamide with a reducing agent, and then cyclizing same under acidic conditions to obtain chiral demethylnicotine; and S5, methylaminating chiral demethylnicotine to obtain chiral nicotine. Said method is simple, easy to operate, has low costs, a high yield and a high ee value, and is suitable for industrial 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/CN2021/112799
Publication Date:
January 19, 2023
Filing Date:
August 16, 2021
Export Citation:
Assignee:
SHENZHEN ZINWI BIO TECH CO LTD (CN)
International Classes:
C07D401/04
Domestic Patent References:
| WO2019037761A1 | 2019-02-28 |
Foreign References:
| CN110256403A | 2019-09-20 | |||
| CN111875620A | 2020-11-03 | |||
| CN112876461A | 2021-06-01 | |||
| CN104341390A | 2015-02-11 | |||
| CN1233829A | 1999-11-03 |
Other References:
SATO, M. ET AL.: "Psychotropic Agents. I. Synthesis of 1-Pyridinyl-1-butanones, 1-Indolyl-1- butanones and the Related Compounds", CHEMICAL AND PHARMACEUTICAL BULLETIN, vol. 26, no. 11, 31 December 1978 (1978-12-31), pages 3296 - 3305, XP001149137
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 55, no. 6, 1990, pages 1736 - 44
JOURNAL OF THE CHEMICAL SOCIETY, vol. 1, no. 2, 2002, pages 143 - 154
JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 46, no. 6, 2009, pages 1252 - 1258
See also references of EP 4144727A4
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 55, no. 6, 1990, pages 1736 - 44
JOURNAL OF THE CHEMICAL SOCIETY, vol. 1, no. 2, 2002, pages 143 - 154
JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 46, no. 6, 2009, pages 1252 - 1258
See also references of EP 4144727A4
Attorney, Agent or Firm:
BEIJING WEIZHENG PATENT AGENCY CO., LTD. (CN)
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