3alpha-Acetylthioandrostane-6alpha,17beta-diol → 3alpha-Acetylthioandrostane-6,17-dione

Participants

Reaction Steps

To a stirred suspension of 3α-acetylthioandrostane-6α,17β-diol (1.40 g) in CH2Cl2 (50 mL), NMNO (1.37 g), TPAP (68 mg) and powdered molecular sieves 4 Å (2.1 g) were added at room temperature. After 2 hrs NMNO (0.7 g), TPAP (34 mg) and molecular sieves 4 Å (1 g) were added again and the reaction was stirred for further 1.5 hrs. The crude product was purified by flash chromatography (SiO2, cyclohexane:EtOAc 7:3) to give 3α-acetylthioandrostane-6,17-dione (1.07 g, 76%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.99 (1H, bb), 2.55-1.20 (23H, m), 0.86 (3H, s), 0.79 (3H, s).

Provenance & Evidence