Hydrogen Peroxide → (S)-4-[(1R,2R)-2-tert-butyl-diphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-2-hydroxy-6-methylmorpholin-3-one

Participants

Reaction Steps

A solution of lithium tri-sec-butylborohydride (1.06 mol) in THF (0.25 ml) was added dropwise to a solution of (S)-4-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-6-methylmorpholine-2,3-dione (95 mg) in THF (3 ml) in a nitrogen atmosphere at −20° C., and the reaction solution was stirred at the same temperature for 30 minutes. A 5 N sodium hydroxide solution (0.03 ml) and 30% aqueous hydrogen peroxide (0.07 ml) were added to the reaction solution, which was then stirred under ice-cooling for one hour. Thereafter, Sodium bisulfite powder (20 mg) was added, and the reaction solution was stirred at room temperature for 30 minutes. Brine was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain 93 mg of the title compound.

Provenance & Evidence