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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 05: 1100 - 1103

DOI: https://doi.org/10.6023/cjoc201211034

Notes

A Practical and Efficient Synthesis of (±)-Rivastigmine

  • Zhang En ,
  • Li Cong ,
  • Zhang Baoyin ,
  • Lü Aiqiao ,
  • Fang Yuan ,
  • Feng Siqi ,
  • Liu Hongmin
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  • New Drug Research & Development Center and School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001

Received date: 2012-11-17

  Revised date: 2013-01-10

  Online published: 2013-01-21

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 81172937, U1204206), the New Teachers' Fund for Doctor Stations, Ministry of Education (No. 20114101120013) and the China Postdoctoral Science Foundation (Nos. 20100480857, 201104402).

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Abstract

A practical and efficient synthesis of (±)-rivastigmine, which is an acetyl cholinesterase inhibitor of the carbamate family and has been approved for the treatment of Alzheimer's disease in more than 60 countries, was developed in three steps from cheap and commercially available 3-ethylphenol. The key step of the synthesis involved the NBS-promoted benzylic bromination of 3-ethylphenyl ethyl(methyl)carbamate. The target molecular was obtained in 71% overall yield without any traditional purification (column chromatography or crystallization). The reactions include esterification, benzylic bromination, substitution reaction.

Key words： rivastigmine; benzylic bromination; 3-ethylphenol; synthesis; Wohl-Ziegler reaction

Cite this article

Zhang En , Li Cong , Zhang Baoyin , Lü Aiqiao , Fang Yuan , Feng Siqi , Liu Hongmin . A Practical and Efficient Synthesis of (±)-Rivastigmine[J]. Chinese Journal of Organic Chemistry, 2013 , 33(05) : 1100 -1103 . DOI: 10.6023/cjoc201211034

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