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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 07: 1573 - 1577

DOI: https://doi.org/10.6023/cjoc201302006

Notes

Synthesis of (2S,3aR,7aS)-Benzyl Octahydro-1H-indole-2-carboxylate

  • Shi Tao ,
  • Shen Jiefeng ,
  • An Qianjin ,
  • Liu Delong ,
  • Liu Yangang ,
  • Zhang Wanbin
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  • a School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240;
    b School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received date: 2013-02-02

  Revised date: 2013-02-21

  Online published: 2013-02-22

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21172143, 21172145, 21232004).

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Abstract

The key intermediate of antihypertensive drugs trandolapril, (2S,3aR,7aS)-benzyl octahydro-1H-indole-2-car-boxylate, was synthesized by improvement of synthetic route and optimation of synthetic technology with satisfactory results (99% ee and 13.2% overall yield). The structure and absolute configuration of the product were characterized by NMR and HPLC analysis, which are completely consistent with the reported data of the literature. It was obvious that the current methodology provided an efficient pathway for the synthesis of trandolapril.

Key words： trandolapril; benzyl octahydro-1H-indole-2-carboxylate; synthesis

Cite this article

Shi Tao , Shen Jiefeng , An Qianjin , Liu Delong , Liu Yangang , Zhang Wanbin . Synthesis of (2S,3aR,7aS)-Benzyl Octahydro-1H-indole-2-carboxylate[J]. Chinese Journal of Organic Chemistry, 2013 , 33(07) : 1573 -1577 . DOI: 10.6023/cjoc201302006

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