(Dimethyl sulfide)trihydroboron → HCID 67406438, compound

Participants

Reaction Steps

In THF (100 ml) was dissolved 3-((2S,4S)-1-(tert-butoxycarbonyl)-4-fluoro-2-pyrrolidinylmethoxy)propionic acid (2.48 g, 8.51 mmol). At room temperature, a 10.0M borane-dimethyl sulfide solution (2.79 ml, 27.9 mmol) was added and the mixture was stirred at room temperature for 3.5 hours and then, at 60° C. for 30 minutes. After cooling to room temperature, the reaction mixture was poured in ice water (100 ml), 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 from chloroform/methanol (20/1) eluate fractions, the title compound (2.84 g, 100%) was obtained as a colorless oil.

Provenance & Evidence