Dimethyl Sulfoxide → HCID 86760351, compound

Participants

Reaction Conditions

Reaction Steps

In methylene chloride (43 ml) were dissolved 3-((2S,4S)-1-(tert-butoxycarbonyl)-4-fluoro-2-pyrrolidinylmethoxy)propanol (2.84 g, 9.30 mmol), triethylamine (7.78 ml, 55.8 mmol) and DMSO (6.61 ml, 93.7 mmol). Under stirring at 0° C., a pyridine-sulfur trioxide complex (4.44 g, 27.9 mmol) was added dropwise to the resulting solution. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 2 hours. Water (50 ml) was added to the residue obtained by distilling off the solvent under reduced pressure, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby hexane/ethyl acetate (4/1) eluate fractions, the title compound (1.35 g, 53%) was obtained as a colorless oil.

Provenance & Evidence