Trifluoroacetic acid → 3-[(3S)-3-Pyrrolidinyloxy]pyridine

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a cold (0-5° C.), stirring solution of 3-((3S)-N-(tert-butoxycarbonyl)-3-pyrrolidinyloxy)pyridine (0.535 g, 2.024 mmol) in dry CH2Cl2 (5 mL, distilled from LiAlH4) was treated drop-wise with trifluoroacetic acid (3 mL, 4.44 g, 38.94 mmol). After stirring 30 min at 0-5° C., the solution was concentrated by rotary evaporation. The residue was acidified with 1 M HCl solution (15 mL) and extracted with toluene (4×25 mL) to remove impurities (triphenylphosphine oxide). At 0-5° C., the aqueous layer was basified with 1 M NaOH solution to pH 12. The mixture was saturated with NaCl and extracted with CHCl3 (8×20 mL). The combined CHCl3 extracts were dried (Na2SO4), filtered, concentrated by rotary evaporation and briefly dried under high vacuum to give 240 mg (72.3%) of a light-yellow oil.

Provenance & Evidence