Acetic Acid → 20,20-Ethylenedioxy-16alpha-methyl-5alpha-pregnane-3alpha,11beta-diol

Participants

Reaction Steps

A solution of sodium borohydride (4.12 g) in water (41 ml) was added to a refluxing solution of 20,20-ethylenedioxy-3α-hydroxy-16α-methyl-5α-pregnan-11-one (7.55 g) in ethanol (375 ml) containing pyridine (7 drops). The mixture was refluxed for 1 hr. then cooled and glacial acetic acid added until no further effervescence occurred. The mixture was partitioned between 3%-aqueous sodium hydrogen carbonate and ethyl acetate. The aqueous portion was extracted with additional ethyl acetate. The combined organic extracts were washed with saturated brine solution, dried and evaporated to a white foam which crystallised from acetone-water to afford the title compound as white prisms (3.29 g),

Provenance & Evidence