Benzaldehyde → 1,1-Dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-[(phenylmethyl)amino]butanoate

Participants

Reaction Steps

1,1-Dimethylethyl (3S)-4-amino-3-[(3-chloro-4-cyanophenyl)amino]butanoate (0.355 g, 1.15 mmol), benzaldehyde (0.12 g, 1.15 mmol), and 4 Å molecular sieves in EtOH (4 mL) were stirred at room temperature for 3 h. To this mixture, NaBH4 (excess amount) was added and the reaction was stirred for additional 1 h. The reaction was filtered. The filtrate was diluted with H2O and extracted with Et2O (2×). The organic extracts were washed with H2O, dried over Na2SO4, filtered, concentrated, and purified via silica gel chromatography with 0% MeOH in CH2Cl2 grading to 5% MeOH in CH2Cl2 to yield the titled product (0.27 g, 59%) as a white solid. LC-MS (ES) m/e 400.3 (M+H)+.

Provenance & Evidence