3-(3-Cyano-phenyl)-2-pyrrolidin-2-ylidene-propionic acid methyl ester → 3-[2-(4,5-Dihydro-3H-pyrrol-2-yl)-ethyl]benzonitrile

Participants

Reaction Conditions

Reaction Steps

A flask containing 3-(3-Cyano-phenyl)-2-pyrrolidin-2-ylidene-propionic acid methyl ester (0.25 g, 0.977 mmol), and H3BO3 (0.0664 g, 1.07 mmol) is heated to 180° C. for 2 h. The reaction is cooled to RT and treated with H20 (0.8 mL) and CH2Cl2 (2 mL) and the resulting mixture is vigorously stirred. The organic phase is separated, diluted with CH2Cl2 (15 mL) dried over Na2SO4 and concentrated. Purification by flash chromatography (2:1:1/EtOAc:CH2Cl2:hexanes) yields the title compound (0.07 g, 0.35 mmol). 1H NMR (CDCl3, 300 MHz) 7.63-7.35(m, 4H), 4.08-3.95(m, 2H), 3.18-3.01(m, 4H), 2.87-2.73(m, 2H), 2.20-2.06(m, 2H).

Provenance & Evidence