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Updated: Jul 16, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
[Synthesis of S-(+)-rivastigmine hydrogentartrate]
Jin Feng1, Wei-Min Chen, Ping-Hua Sun
1Department of Medicinal Chemistry, School of Pharmacy, Jinan University, Guangzhou 510632, China.
Objective:
To optimize the synthetic procedure of S-(+)-rivastigmine hydrogentartrate which was known as an agent for the treatment of Alzheimer disease.
Methods:
S-(+)-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.
Results:
The total yield of S-(+)-rivastigmine hydrogentartrate was 4.17%.
Conclusion:
The materials in this procedure are all commercially available. The reaction conditions are mild and total yield is high.
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