Water → L-Prolinanilide

Participants

Reaction Steps

To a solution of (S)-(+)-N-Boc-2-phenylaminocarbonylpyrrolidine (1.1 g, 3.8 mmol) in 5 mL of CH2Cl2 at 0° C. was added 5 mL of TFA dropwise over 1 hour. The solution was warmed to room temperature and stirred for 1.5 hours. To the reaction mixture was added 100 mL of water and the aqueous layer was washed with EtOAc. The aqueous layer was then made basic with 30 mL of 10% NaOH and extracted therein with 20 mL EtOAc. The organic layer was then dried over Na2SO4, filtered and concentrated under reduced pressure to give a white solid (0.40 g, 56%). ES (+) MS m/e=191 (M+H).

Provenance & Evidence