HCID 13990933, compound → HCID 13990935, compound

Participants

Reaction Steps

A solution of 3.0 g. of lithium tri-(tert.-butoxy)-aluminum hydride in 15 ml. of tetrahydrofuran is introduced into 2.0 g. of 11β-fluoro-4-androstene-3,17-dione in 5 ml. of tetrahydrofuran. After 45 minutes, the solution is poured into sulfuric ice water and extracted with methylene chloride. The crude product (1.5 g.) representing a mixture of 11β-fluoro-17β-hydroxy-4-androsten-3-one and 11β-fluoro-4-androstene-3β,17β-diol is stirred for 4 hours at room temperature with 1.8 g. of 2,3-dichloro-4,5-dicyano-1,4-benzoquinone in 50 ml. of dioxane. The solution is diluted with ether, washed repeatedly with 2N sodium hydroxide solution and water, and dried over sodium sulfate. After chromatography on silica gel with acetone/hexane, 1.2 g. of 11β-fluoro-17β-hydroxy-4-androsten-3-one is obtained; m.p. 160°-162°. UV: ε239 = 16,500 (methanol).

Provenance & Evidence