Water → HCID 24862304, compound

Participants

Reaction Steps

In an argon atmosphere, N-(benzoxazole-2-yl)-N-(3-(4-methoxyphenoxy)propyl)-3-hydroxybenzylamine (200 mg) was dissolved in dichloromethane (1.5 mL), and triethylamine (0.11 mL) was added dropwise to the solution at room temperature, followed by stirring for 5 minutes at the same temperature. Subsequently, a solution of (S)-2-trifluoromethanesulfonyloxybutyrolactone (174 mg) in dichloromethane (1 mL) was added dropwise to the mixture over 10 minutes at room temperature, followed by stirring for 5 hours at the same temperature. The reaction mixture was added to water (50 mL), and the mixture was extracted with ethyl acetate (30 mL×3). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate anhydrate and concentrating under reduced pressure. The residue was purified through silica gel column chromatography (n-hexane/ethyl acetate=1/1), to thereby yield a colorless oil (242 mg, 100′, 98.1% ee).

Provenance & Evidence