4-Methylmorpholine → (S)-2-(dibenzylamino)-N-methoxy-N-methylbutanamide

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of argon, (S)-2-(dibenzylamino)butanoic acid (27 g, 80.0 mmol, Eq: 1.00) was combined with dichloromethane (250 ml) to give a white suspension. At 0° C., TBTU (36.0 g, 112 mmol, Eq: 1.4) was added. The reaction was stirred for 2 h at 0° C. Then N-methylmorpholine (24.3 g, 26.4 ml, 240 mmol, Eq: 3) and N,O-dimethylhydroxylamine hydrochloride (19.5 g, 200 mmol, Eq: 2.5) were added. The reaction was stirred overnight at RT. The reaction mixture was extracted with water (2×75 ml) and brine (50 ml). The organic layers were dried over Na2SO4 and concentrated in vacuo. The residual solvent was removed under vacuum. The title compound was obtained as a light yellow oil (35.5 g, 95.1%, MS (m/e)=327.3 [M+H+]).

Provenance & Evidence