Acetic Acid → (S)-methyl 2-((4-methoxybenzyl)amino)-2-phenylacetate

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-methyl 2-amino-2-phenylacetate (1.0 g, 6.06 mmol) in anhydrous MeOH (20 mL) was added 4-methoxy benzaldehyde (0.82 g, 6.06 mmol) and few drops of HOAc. After 30 min, the reaction mixture was cooled to 0° C., NaBH4 (0.69 g, 12.12 mmol) was added and the contents were stirred at ambient temperature. After 2 h, the reaction was quenched with ice cold H2O (10 mL), MeOH was removed under reduced pressure and the organic contents were extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine (1×20 mL), dried over Na2SO4, concentrated and (S)-methyl 2-((4-methoxybenzyl)amino)-2-phenylacetate thus obtained was taken directly for step 2. MS: [M+H]+ m/z 286.

Provenance & Evidence