Triethylamine → (R)-1-[4-(4-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methylamide

Participants

Reaction Steps

A solution of 1.82 mmol of (R)-1-[4-(4-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid in 37 ml of N,N-dimethylformamide was cooled to 0° C., was treated consecutively with 2.0 mmol of triethylamine, 1.82 mmol of HBTU, 2.2 mmol of methylamine hydrochloride, and 2.0 mmol of triethylamine. The ice-bath was removed, and stirring continued at RT. The reaction was stopped after 30 min, and the orange coloured solution was evaporated under reduced pressure. The residue obtained was triturated in 1 ml of ethyl acetate; the white solid product was filtered, thereafter dissolved in dichloromethane; and the solution washed three times with water. The organic phase was dried over sodium sulfate, then evaporated under reduced pressure to yield 409 mg (66% of theory) of the (R)-1-[4-(4-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methylamide a white solid. MS: m/e=343 (M+H)+; enantiomeric excess >99.5%.

Provenance & Evidence