Water → HCID 86735822, compound

Participants

Reaction Steps

To a mixture of 1-molar diborane-tetrahydrofuran complex (not stabilized with sodium borohydride, 157 ml) and lithium borohydride (3.4 g, 0.155 mole) cooled in an ice bath was added dropwise over about 25 minutes a solution of 1α,2α-epoxy-25-hydroxy-6β-methylsulfonyloxy-5α-cholestan-3-ol (20.0 g, 0.392 mole) in tetrahydrofuran (100 ml) with stirring under nitrogen. The suspension was stirred at 0° for about 6 hours, and then stored in a refrigerator (ca. 30° C) overnight. Water (200 ml) was added cautiously to the reaction mixture cooled in an ice bath. An additional 200 ml of water was added to the turbid solution and the solution was extracted with methylene chloride. The layers were separated and the organic phase was washed successively with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and filtered. Evaporation of the filtrate gave 22 g of 1α,25-dihydroxy-6β-methylsulfonyloxy-5α-cholestan-3-ol as a white foam.

Provenance & Evidence