Acetic Acid → 17beta-Cyano-17alpha-hydroxy-16beta-methylandrosta-1,4,9(11)-trien-3-one

Participants

Reaction Steps

16β-Methylandrosta-1,4,9(11)-triene-3,17-dione (U.S. Pat. No. 3,010,958, 12.0 g) and potassium cyanide (7.909 g) are suspended in methanol (24 ml). The resulting slurry is then treated with glacial acetic acid (3.5 ml) and allowed to stir in a tightly stoppered flask at 20°-25° for 72 hr. TLC (acetone/methylene chloride, 4/96). The reaction mixture is then cooled to 0° and quenched with glacial acetic acid (4.2 ml). The solids are then collected by filtration, triturated with methanol/water (1/1, 3×10 ml) and dried by heating (60°) under reduced pressure (60 mm) to obtain the title compound, m.p. 241°-247.5°; NMR (CD2Cl2) 1.32, 1.42, 5.58, 6.08, 6.30 and 7.25 δ.

Provenance & Evidence