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Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (07): 1573-1577.DOI: 10.6023/cjoc201302006 Previous Articles     Next Articles

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(2S,3aR,7aS)-八氢-1H-吲哚-2-甲酸苄酯的合成

时涛a, 申杰峰a, 安前进a, 刘德龙a, 刘燕刚a, 张万斌a,b   

  1. a 上海交通大学药学院 上海 200240;
    b 上海交通大学化学化工学院 上海 200240
  • 收稿日期:2013-02-02 修回日期:2013-02-21 发布日期:2013-02-22
  • 通讯作者: 刘德龙, 张万斌 E-mail:wanbin@sjtu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 21172143, 21172145, 21232004)资助项目.

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

Shi Taoa, Shen Jiefenga, An Qianjina, Liu Delonga, Liu Yanganga, Zhang Wanbina,b   

  1. a School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240;
    b School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
  • Received:2013-02-02 Revised:2013-02-21 Published:2013-02-22
  • Supported by:

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

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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