Dimethylformamide → HCID 66652820, compound

Participants

Reaction Conditions

Reaction Steps

To 4-[(1R)1-aminoethyl)]benzonitrile (Haoyuan Chemexpress, 3.4 g; 23 mmol) in DMF (34 mL) was added sodium bicarbonate (3.9 g; 46 mmol) and methyl 2-bromopropionate (2.8 mL; 25 mmol). The reaction mixture was stirred at 75° C. overnight. EtOAc was added to the reaction mixture and the organic phase was washed 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-[(1R)-1-(4-cyanophenyl)ethyl]-D-alaninate (first eluting compound) as a white solid (2.1 g, 40%) and methyl N-[(1R)-1-(4-cyanophenyl)ethyl]-L-alaninate (second eluting compound) as an orange solid (2.3 g, 43%).

Provenance & Evidence