Triethylamine → (R)-1-acryloyl-pyrrolidine-2-carboxylic acid benzyl ester

Participants

Reaction Steps

To a stirred solution of 390 mg (1.6 mmol) D-Proline benzyl ester hydrochloride and 0.47 ml (3.4 mmol) triethylamine in 20 ml dichloromethane at 0° C. was added dropwise 0.2 ml (2.4 mmol) acryloyl chloride and stirring continued for 24 h at room temperature. The reaction mixture was then washed sequentially with water, 1 M hydrochloric acid and once more with water, and the aqueous phases back-extracted with dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to afford 420 mg (100%) of the title compound as a colorless oil. MS m/e (%): 259 (M+, 25), 124 (100), 91 (25), 70 (21).

Provenance & Evidence