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Citation: WANG Li, ZHU Cui-Hong, ZHANG Xiang-Wen, MI Zhen-Tao. Synthesis of 3β-Hydroxy-16α,17α,21-trimethyl-5-en-20-one[J]. Chinese Journal of Applied Chemistry, ;2002, 19(12): 1189-1191. shu

Synthesis of 3β-Hydroxy-16α,17α,21-trimethyl-5-en-20-one

1.
a School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072;
2.
b Tianjin Pharmaceuticals Corp. Ltd., Tianjin

Corresponding author: WANG Li,
Received Date: 29 May 2002
Available Online: 3 September 2002
Fund Project: 天津药业有限公司博士后科研基金资助(199902) (199902)

3U-Hydroxy-16T,17T,21-trimethyl-5-en-20-one was synthesized from 3T-acetoxypregna-5,16-dien-20-one and characterized by elemental analysis, ¹H NMR, MS and IR. 16T,17T-Dimethyl steroid was formed by treatment of 3U-acetoxypregna-5,16-dien-20-one with methylmagnesium bromide, followed by reaction of the resulting 17(20)-enolate with methyl iodide. The main by-products were 3U-hydroxy-16T,17T-dimethyl-5-en-20-one. LHDMS([(CH₃)₃Si]₂NLi) and LDA([(CH₃)₂CH]₂NLi) were chosen as proper reagents for 21-position alkylation. The almost quantitative conversion of 16T,17T-dimethyl corticosteroid was achieved and the highest yield of the 16T,17T,21-trimethyl corticosteroid was 78%. The optimum reaction temperature was -20℃ for 16T,17T-dialkylation and was -50℃ for 21-position alkylation.
- corticosteroid,
- alkylation,
- conjugate addition,
- Rimexolone
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