Water → HCID 13686447, compound

Participants

Reaction Steps

To a solution of the fluoroketone (3) (270 mg) in THF (24 ml) was added sodium borohydride (90 mg) in methanol (6 ml) at room temperature and the mixture was stirred at room temperature for 1 hr. To the reaction mixture were added water and ethyl acetate and the excess reagent was quenched with 2N-HCl. The organic phase was washed with saturated NaHCO3 and brine, and dried over MgSO4. The crude mixture obtained upon evaporation of the solvent was separated by column chromatography on silica gel (10 g). Elution with benzene-ethyl acetate 10:1 gave 6β-acetoxy-2α-fluoro-3α-hydroxycholestane (5) 54 mg, 2%), mp 148°-150° (CHCl3 -MeOH); δ0.79(3H, s, 18-H3), 2.20(3H, s, acetyl), 4.22(1H, m, W1/2 =13 Hz, 3β-H), 4.65(1H, m, 2β-H), and 4.98(1H, m, 6α-H); m/z, 404 (M+ -AcOH), 389,384, 371 and 369.

Provenance & Evidence