Methyl 1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene-20-carboxylate (70 mg) was added to a suspension of 10 mg of lithium aluminum hydride in 5 ml of tetrahydrofuran with ice cooling and the mixture was stirred with ice cooling for 30 minutes. The resulting reaction mixture was diluted with diethyl ether and the excess reducing agent was decomposed with a saturated aqueous solution of sodium sulfate. The insoluble matter was filtered off and washed well with ethyl acetate. The filtrate and washings were combined and concentrated. The residue was washed with cold diethyl ether to give 58 mg of 20-methylpregna-5,7-diene-1α,3β,21-triol.
