Dehydroepiandrosterone → 3beta-Hydroxy-5alpha,6alpha-epoxyandrostane-17-one

Participants

Reaction Steps

To a stirred solution of 3β-hydroxyandrost-5-en-17-one (0.81 g) in CH2Cl2 (7.4 mL) cooled at 0° C., a solution of mCPBA (0.77 mg) in CH2Cl2 (13.6 mL) was added dropwise. After 0.5 h at 0° C. and 0.5 h at room temperature, a 10% aqueous solution of Na2SO3 was added. The mixture was neutralized by addition of 5% NaHCO3 solution and extracted with CH2Cl2 (3×100 mL). The combined organic extracts were washed with H2O, dried over Na2SO4, and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20) to give 3β-hydroxy-5α,6α-epoxyandrostan-17-one (0.64 g, 75%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.62 (d, 1H), 3.52 (m, 1H), 2.87 (d, 1H), 2.44-0.56 (m, 19H), 1.00 (s, 3H), 0.72 (s, 3H).

Provenance & Evidence