Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (9): 2430-2434.DOI: 10.6023/cjoc201704009 Previous Articles     Next Articles

Notes

利用过二硫酸盐氧化消除2-碘双氢非那雄胺制备非那雄胺

毛冀川a, 申玉良b, 曹春雨b, 舒志坚b, 郑良彬b, 许新华a   

  1. a 湖南大学化工学院 长沙 410082;
    b 湖南玉新药业有限公司 邵阳 422000
  • 收稿日期:2017-04-08 修回日期:2017-05-09 发布日期:2017-05-17
  • 通讯作者: 许新华 E-mail:xhx1581@hnu.edu.cn
  • 基金资助:

    湖南省科技重大专项(No.2014FJ1010)资助项目.

Preparation of Finasteride via Oxidative Elimination of 2-Iododihydrofinasteride by Using Peroxydisulfates as Oxidizing Agents

Mao Jichuana, Shen Yuliangb, Cao Chunyub, Shu Zhijianb, Zheng Liangbinb, Xu Xinhuaa   

  1. a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    b Limited Liability Company of Yu Xin Phamacy, Shaoyang 422000
  • Received:2017-04-08 Revised:2017-05-09 Published:2017-05-17
  • Contact: 10.6023/cjoc201704009 E-mail:xhx1581@hnu.edu.cn
  • Supported by:

    Project supported by the Important Science & Technology Specific Projects in Hunan Province (No. 2014FJ1010).

The influence of various bases and oxidizing agents to the oxidation elimination of 2-iododihydrofinasteride (2a) was explored, and the results showed that K2S2O8 is the best oxidizing agent. The influences of solvents, amount of K2S2O8, temperature and reaction time on the oxidation elimination were also investigated, and the optimal conditions were obtained as follow:tetrahydrofuran (THF), 10 h, room temperature, nK2S2O8:n2a=2:1. Finasteride 3a was obtained in the yield of 96.3% with the purity of 99.6%, when the reaction was performed under optimal conditions. The optimal conditions are also suitable for the oxidation elimination of 2-iodo-3-oxo-4-aza-5α-androstane-17β-carboxylic acid (2b) and 2-iodo-3-oxo-4-aza-5α-androstane-17β-carboxylate (2c), for giving the desired products in good yield and high purity. Other advantages include mild conditions, excellent yields, high purity and friendly to environment.

Key words: finasteride, peroxydisulfate, oxidation elimination, 2-iododihydrofinasteride