1,2-Dichloroethane → (2S,3S)-N-cyclopropyl-3-(dibenzylamino)-2-hydroxypentanamide

Participants

Reaction Steps

Under an atmosphere of argon, (2S,3S)-3-(dibenzylamino)-2-hydroxypentanoic acid (5.85 g, 18.7 mmol, Eq: 1.00), cyclopropanamine (2.13 g, 2.62 ml, 37.3 mmol, Eq: 2) were combined with dichloromethane (100 ml) to give a light yellow solution. At 0° C. HOBt (4.29 g, 28.0 mmol, Eq: 1.5), EDC (5.37 g, 28.0 mmol, Eq: 1.5) and N-methylmorpholine (3.78 g, 4.1 ml, 37.3 mmol, Eq: 2) were added to the reaction. The reaction was stirred overnight at RT. The reaction mixture was poured into water (150 ml) and extracted with dichloromethane. The organic layer was back-extracted with water. The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 70 g, 0% to 60% ethyl acetate in heptane). The title compound was obtained as a light brown crystalline (4.42 g, 67.2%, MS (m/e)=353.3 [M+H+]).

Provenance & Evidence