Citation: Qin Jian ZHAO, Zhen Su LI. SELECTIVE REDUCTION OF 3,17-DIOXO-STEROIDS TO 17β-HYDROXY-3-OXO-STEROIDS[J]. Chinese Chemical Letters, ;1993, 4(6): 479-482. shu

SELECTIVE REDUCTION OF 3,17-DIOXO-STEROIDS TO 17β-HYDROXY-3-OXO-STEROIDS

Department of Medicinal Chemistry, Beijing Medical University, Beijing 100083

Received Date: 6 January 1993

11β-Hydroxy-androst-4-en-3,17-dione (1a),androst-4,9 (11)-dien-3,17-dione-(2a),androst-4-en-3,11,17-trione (3a),11α-methoxy-androst-4-en-3,17-dione (4a) and 11β-metboxy-androst-4-en-3,17-dione (5a) were selectively reduced to the corresponding 17β-OH derivatives in one step without the protection of 3-oxo (and 11-oxo,in the case of 3a) group with the yields ranging from 65% to 79%.In these reactions,the ditute NaBH₄ (or KBH₄) solution in methanol was added dropwise to the 3,17-dioxo-steroids solution in methanol-benzene-pyridine,while the reaction mixtures were well stirred at -5~5℃.Acid (such as gtacial acetic acid) was added to quench the reactions.The resulted testosterone derivatives (1b~5b) were purified by flash chromatography.
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