Water → (S)-3-benzyloxymethylisothiazolidine 1,1-dioxide

Participants

Reaction Steps

A mixture of (S)-2-amino-3-benzyloxy-1-propanol (5.0 g) and triethylamine (7.9 mL) was dissolved in tetrahydrofuran (40 mL), methanesulfonyl chloride (4.4 mL) was added under ice-cooling, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, the organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was dissolved in N,N-dimethylformamide (10 mL), sodium chloride (3.2 g) was added, and the mixture was stirred at 80° C. for 5 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. A mixture of the obtained residue and 1,10-phenanthroline (28 mg) was dissolved in tetrahydrofuran (80 mL), diisopropylamine (3.9 mL) was added at −70° C., and n-butyllithium (38 mL) was further added. The reaction mixture was heated to room temperature, and stirred overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, the organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (4.49 g).

Provenance & Evidence