Tetrahydrofuran → HCID 68730133, compound

Participants

Reaction Steps

To a stirred solution of 3,3-ethylenedioxy-4,4-dimethyl-5-androsten-17β-ol (190 mg) in THF (3.5 ml) at 0° C., under N2, 1M BH3.THF complex in THF (3.3 ml) was added in five portions over 5 days. The reaction mixture was cautiously quenched by dropwise addition of H2O at 0° C. (1.5 ml), followed by 4N NaOH (0.16 ml) and by 30-32 wt. % H2O2 solution in water (0.056 ml). After 24 h, EtOAc and brine were added, the phases were separated and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (SiO2, n-hexane/DCM/acetone 80/10/10) to give 3,3-ethylenedioxy-4,4-dimethylandrostan-5α,17β-diol (80 mg, 23%).

Provenance & Evidence