Synthesis of S-(+)-rivastigmine hydrogentartrate.
- Author:
Jin FENG
1
;
Wei-Min CHEN
;
Ping-Hua SUN
Author Information
- Publication Type:Journal Article
- MeSH: Cholinesterase Inhibitors; chemical synthesis; chemistry; Models, Chemical; Molecular Structure; Phenylcarbamates; chemical synthesis; chemistry; Rivastigmine; Stereoisomerism
- From: Journal of Southern Medical University 2007;27(2):177-180
- CountryChina
- Language:Chinese
-
Abstract:
OBJECTIVETo optimize the synthetic procedure of S-(+)-rivastigmine hydrogentartrate which was known as an agent for the treatment of Alzheimer disease.
METHODSS-(+)-rivastigmine hydrogentartrate was synthesized by using 1-(3-hydroxyphenyl)ethanone as the starting material via oximation, reduction and N-methylation to produce the key intermediate 3-1-dimethylaminoethylphenol, which finally reacted with N-ethyl-N-methylcarbamoyl chloride. The enantiomers were resolved with di-(+)-p-toluoyl-D-tartaric acid, and the title compound was prepared by mixing S-rivastigmine base with L-(+)-tartrate.
RESULTSThe total yield of S-(+)-rivastigmine hydrogentartrate was 4.17%.
CONCLUSIONThe materials in this procedure are all commercially available. The reaction conditions are mild and total yield is high.