p-Toluenesulfonic acid monohydrate → HCID 70145156, compound

Participants

Reaction Steps

17,17-Ethylenedioxy-androst-5,15(16)-dien-3β-ol from Example 28B or otherwise obtained is dissolved in acetone (500 mL) and water (60 mL) and the solution is cooled to 0° C. To the 0° C. solution is added p-toluenesulfonic acid monohydrate (1.000 g, 5.257 mmol). The 0° reaction mixture is stirred for 5 hours and then stored at 40° for 16 hours. The chilled reaction solution is diluted with water (300 mL) and acetone is evaporated under reduced pressure. The aqueous slurry remaining is extracted with EtOAc (2×300 mL) and the combined organic phases are washed with saturated aqueous NaHCO3 (200 mL) and brine (200 mL), dried over MgSO4, filtered and concentrated. The residue is purified by flash chromatography (1:1 EtOAc/CH2Cl2) to afford 3-hydroxy-androst-5,15(16)-dien-17-one (C3-alcohol).

Provenance & Evidence