Benzoyl chloride → methyl 1-benzoylpyrrolidine-2-carboxylate

Participants

Reaction Steps

Benzoyl chloride (1.40 mL, 12.1 mmol) was added in a dropwise manner to a mixture of L-proline methyl ester hydrochloride (2.00 g, 12.1 mmol) and Et3N (4.20 mL, 30.2 mmol) in CH2Cl2 (40 mL) and the resulting mixture stirred overnight at rt. The mixture was concentrated in vacuo and the residue treated with water and extracted with EtOAc and the combined extracts dried over Na2SO4. Concentration left a residue which was loaded onto a silica gel column and eluted with MeOH/CH2Cl2 which allowed for isolation of 2.76 g (94%) of the title compound as a white solid. MS(ES): (M+1)+ 234.2 m/z.

Provenance & Evidence