Trifluoroacetic acid → HCID 54443836, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(fluoromethyl)acrylate (2.54 g, 19.2 mmol) and N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine (5.1 mL, 19.2 mmol) in dichloromethane (15 mL) cooled to 0° C. in an ice bath, was added 1M solution of TFA in dichloromathane (1.8 mL), and the resulting mixture stirred at 0-2° C. for 75 minutes. The reaction was diluted with dichloromethane (20 mL) and washed with saturated sodium bicarbonate solution, brine and dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Biotage 40M; 10% ethyl acetate/hexanes) to afford ethyl 1-benzyl-3-(fluoromethyl)pyrrolidine-3-carboxylate (2.98 g, 58%).

Provenance & Evidence