Benzylamine → 3-Amino-1-benzylpyrrolidine-3-carbonitrile

Participants

Reaction Steps

To a solution of 2-hydroxy-4-methyl-pentanoic acid (1-benzyl-3-cyano-pyrrolidin-3-yl)-amide (0.315 g, 1.0 mmol) in dry THF (27 mL) was added DMAP (0.171 g, 1.4 mmol), p-nitrophenyl chloroformate (0.221 g, 1.1 mmol), and N-methylmorpholine (0. 121 mL, 1.1 mmol). The resulting mixture was allowed to stir overnight (20 h) under argon at room temperature, then treated with benzylamine (0.150 g, 1.4 mmol) and allowed to stir overnight (24 h). When the reaction was complete, the mixture was diluted with EtOAc (50 mL), then washed sequentially with saturated aq. NaHCO3 (50 mL), water and brine, dried over Na2SO4, filtered and concentrated to give 0.180 g (40% yield ) of the desired product after purification by prep-HPLC; 1H NMR (CDCl3) 7.25 (10H, m), 6.25 (1H, s), 5.4-5.1 (2H, m), 4.45 (2H, m), 3.65 (2H, m), 3.1-3.0 (1H, m), 2.98-2.57 (5H, m), 2.16 (1H, m), 1.73 (2H, m), 0.9 (6H, m). MS, m/z 449=M+1.

Provenance & Evidence