Water → (S)-1-benzyl-3-fluoropyrrolidine

Participants

Reaction Steps

To a solution of (R)-1-benzyl-3-pyrrolidinoltosylate (3.06 g, 9.24 mmol) in THF (30 ml) was added 1.0M solution of tetrabutylammonium fluoride in THF (37.0 ml, 37.0 mmol) at room temperature. After 1.5 h stirring at reflux temperature, water (150 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate (100 ml×2). The combined extract was washed with water, brine, dried (Na2SO4), and concentrated to give brown oil, which was purified by column chromatography (silica gel: 80 g, CH2Cl2/MeOH:50/1) to afford 1.18 g (71%) of brown oil.

Provenance & Evidence