ethyl (E)-3beta,14beta-dihydroxy-21-methyl-5beta-pregn-20-ene-21-carboxylate → (E)-21-hydroxymethyl-21-methyl-5beta-pregn-20-ene-3beta,14beta-diol

Participants

Reaction Steps

To a solution of 9.60 g of ethyl (E)-3β,14β-dihydroxy-21-methyl-5β-pregn-20-ene-21-carboxylate (Boutagy J. and Thomas R., Aust. J. Pharm, Chem., 1972, NS1, 67) in 370 ml of dry tetrahydrofuran, 104 ml of 1M i-Bu2AlH in hexane were added dropwise under nitrogen at -78° C. After 2 hrs the reaction was quenched with a solution of 46.0 g of sodium sulfate in 350 ml of water and stirred at room temperature for 2 hours. The mixture was then filtered through Celite and washed with methylene chloride. The organic layer was separated, dried over anhydrous sodium sulfate and evaporated to dryness to give 8.30 g of (E)-21-hydroxymethyl-21-methyl-5β-pregn-20-ene-3β,14β-diol as an off-white solid.

Provenance & Evidence