HCID 21722881, compound → 14alpha-Fluoro-3beta-hydroxy-5alpha-androstan-17-one

Participants

Reaction Steps

14α-Fluoro-3β-hydroxyandrost-5(6)-en-17-one (400 mg) in ethanol (70 ml) was hydrogenated over palladium-charcoal (5%; 250 mg) until uptake of hydrogen ceased (72 hr). The solvent was evaporated in vacuo and the crude product was recrystallised from acetone: hexane to give prisms of 14α-fluoro-3β-hydroxy-5α-androstan-17-one (158 mg) m.p. 201°-202°; [α]D23 +83° (c 0.84, CHCl3); vmax 3500 and 1730 cm-1 ; the PMR spectrum included signals at δ0.83 (3H, s, 19-Me), 1.00 (3H, s, 18-Me) and 3.6 (1H, m, 3-CHOH); FMR φ*+164 ppm (broad multiplet ca 80 Hz wide).

Provenance & Evidence