An Efficient Strategy for Large Scale Asymmetric Synthesis of Rivastigmine Tartarate

Document Type : Research Paper

Authors

Chemistry Department, Payame Noor University (PNU), P. O. Box 19395-4697 Tehran, I. R. of IRAN.

Abstract

An efficient process for the large scale synthesis of Rivastigmine tartarate, one of the most potent drugs for the treatment of mild-to-moderate dementia of the type presenting in Alzheimer’s disease, has been developed. Recent approaches are based on lipase catalyzed kinetic resolution, chemoenzymatic asymmetric synthesis and asymmetric transfer hydrogenation. In this study, a high yielding stereoselective and short synthesis of (S)-Rivastigmine tartarate is described with an overall isolated yield of 63%. All the starting reagents and catalysts are inexpensive and commercially available. The reported strategy afforded in presence of Nano-K2CO3 via four steps, which (to the best of our knowledge) depicts the shortest method to enantiopure Rivastigmine tartarate reported to date. It is noteworthy that purification of Rivastigmine compound was achieved by simple extraction and washing operations under different pH values. Finally L-(+‏)-Tartaric acid was added to Rivastigmine in acetone. The mixture was heated to reflux. It crystallized dried easily.

Keywords

References

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Semiannual Organic Chemistry Journal
Volume 1, Issue 2
October 2022
Pages 64-70

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History

  • Receive Date: 06 July 2018
  • Revise Date: 29 September 2022
  • Accept Date: 16 September 2018

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