Benzaldehyde → N-Benzylglycine ethyl ester

Participants

Reaction Steps

To a solution of benzaldehyde (14.0 g, 0.132 mol) in absolute EtOH (500 mL) was added glycine ethyl ester hydrochloride (37.0 g, 0.256 mol), NaOAc (32.5 g, 0.396 mol) and sodium cyanoborohydride (9.8 g, 0.158 mol), and the resulting mixture heated to reflux. After 1 hr at reflux, the reaction was cooled and concentrated in vacuo. The residue was taken up into 1N NaOH and EtOAc. The layers were separated and the organic phase was washed with 1N NaOH, brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was taken up into EtOAc (150 mL) and treated with gaseous HCl. The resulting solid was collected, washed with Et2O and dried to provide 23.4 g of compound 701 as the HCl salt. ##STR80##

Provenance & Evidence