Dimethylformamide → HCID 66652869, compound

Participants

Reaction Conditions

Reaction Steps

To 4-[(1S)-1-aminoethyl)]benzonitrile (Haoyuan Chemexpress, 1 g; 6.8 mmol) in DMF (15 mL) was added sodium bicarbonate (1.2 g; 14 mmol) and methyl 2-bromopropionate (0.84 mL; 7.5 mmol). The reaction mixture was stirred at 75° C. overnight. EtOAc was added and the organic phase was washed with three times with H2O and once with brine, organic layer was then dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography (EtOAc/Heptane gradient from 5:95 to 25:75), affording methyl N-[(1S)-1-(4-cyanophenyl)ethyl]-L-alaninate (first eluting compound) as a pale yellow solid (480 mg; 30%) and methyl N-[(1S)-1-(4-cyanophenyl)ethyl]-D-alaninate (second eluting compound) as a yellow solid (470 mg; 30%).

Provenance & Evidence