HCID 11266833, compound → 3beta,17beta-Dihydroxyandrostan-6-one

Participants

Reaction Conditions

Reaction Steps

To a solution of androstane-3β,6α,17β-triol (3.00 g) in CH2Cl2/acetone/—H2O (300/150/6 mL), activated MnO2 (30.0 g, 345 mmol) was added in three portions over 8 h. The mixture was stirred at 45° C. overnight. After cooling to room temperature, the mixture was filtered through Celite. The filtrate was evaporated and the residue was purified by flash chromatography (SiO2, CH2Cl2/n-n-hexane/i-PrOH 10/5/1) to give 3β,17β-dihydroxyandrostan-6-one (0.89 g, 30%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.54 (d, 1H), 4.48 (d, 1H), 3.45 (m, 1H), 3.30 (m, 1H), 2.27 (dd, 1H), 2.08-0.90 (m, 19H), 0.62 (s, 3H), 0.61 (s, 3H).

Provenance & Evidence