Chinese Journal of Organic Chemistry >
Preparation of Finasteride via Oxidative Elimination of 2-Iododihydrofinasteride by Using Peroxydisulfates as Oxidizing Agents
Received date: 2017-04-08
Revised date: 2017-05-09
Online published: 2017-05-17
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.
Mao Jichuan , Shen Yuliang , Cao Chunyu , Shu Zhijian , Zheng Liangbin , Xu Xinhua . Preparation of Finasteride via Oxidative Elimination of 2-Iododihydrofinasteride by Using Peroxydisulfates as Oxidizing Agents[J]. Chinese Journal of Organic Chemistry, 2017 , 37(9) : 2430 -2434 . DOI: 10.6023/cjoc201704009
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