Sodium borohydride → HCID 66910182, compound

Participants

Reaction Steps

To a stirred solution of 6α-acetoxyandrostane-3,17-dione (5.57 g) in MeOH (188 mL), at 0° C. under N2, NaBH4 (615 mg) was added in portions over 15 min. After stirring for 1.5 h at room temperature, the mixture was quenched by careful addition of H2O (200 mL). MeOH was evaporated and the concentrated solution was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated to dryness. The mixture was purified by flash chromatography (SiO2, cyclohexane/Et2O/acetone 60/20/20) to give 6α-acetoxyandrostane-3β,17β-diol and 6α-acetoxyandrostane-3α,17β-diol (90/10 mixture, 5.30 g, 95%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.55 (m, 1H), 4.49 (bb, 1H), 4.43 (bb, 1H), 3.41 (m, 1H), 3.28 (m, 1H), 1.97 (s, 3H), 1.88-0.82 (m, 19H), 0.79 (s, 3H), 0.64 (m, 1H), 0.61 (s, 3H).

Provenance & Evidence