Diethyl Ether → (S)-1-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]propan-2-ol

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A diethylether solution (1 mL) of (S)-(−)-propylene oxide (0.1 mL) and (1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamine (212 mg) was added to a diethylether suspension (1 mL) of lithium perchlorate (750 mg). The resulting reaction solution was stirred in nitrogen atmosphere at room temperature overnight, and then methylene chloride and iced-water were added thereto. The resulting mixture was stirred. The organic layer was separated, and the water layer was re-extracted with methylene chloride. The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (heptane: ethyl acetate=9:1 to 4:1) to give 172 mg of the title compound. The physical property values of this compound were as follows:

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