Androstenedione → (17alpha)-17-Hydroxy-3-oxoandrost-4-ene-17-carbonitrile

Participants

Reaction Steps

Acetone cyanohydrin (82 ml), potassium cyanide (1 gm) and water (2 ml) are added to a slurry of androst-4-en-3,17-dione (0.80 g) in methanol (400 ml) and water (40 ml) at 35°. The reaction becomes homogeneous and on continued stirring a heavy slurry develops. After 3 hours, 120 ml of water is added dropwise, and the slurry allowed to stir overnight at 20°-25°. The slurry is then cooled in an ice bath, filtered, and the solids washed with methanol/water (1/1). The solvents are dried under reduced pressure to give 70.4 g of the title compound. An additional 13.17 g of product is isolated from the mother liquor on partial evaporation, m.p.=159°-160.5°; [α]D (c=1, CHCl3)=+145.9°; MS=313, 298, 286, 245 and 124 m/e; NMR (CDCl3)=1.00, 1.20, 3.5 and 5.72 δ

Provenance & Evidence