Hydrochloric Acid → (2R)-N-(Benzyloxy)-2-(hydroxymethyl)hexanamide

Participants

Reaction Conditions

Reaction Steps

To a 3000 mL roundbottom flask was added (2R)-2-(hydroxymethyl)hexanoic acid (5) (77 g, 0.527 mol) in THF/water (4:1, 1800 mL), followed by benzylhydroxylamine hydrochloride (100 g, 0.632 mol). The mixture was cooled to 0° C. and was adjusted with 1 N HCl to pH ˜4.5. EDCI (202 g, 1.05 mol) was added in one portion. The mixture was stirred at 0° C. for 2 h, while the pH of the mixture was maintained at ˜4.5 by addition of 1 N HCl. THF was then removed under vacuum, and the white solid was collected by filtration to afford the titled compound as a crude mixture (100 g). Further purification by flash column eluting with ethyl acetate/petroleum ether (1:10) provided the pure product (52 g, 39%). LCMS: (M+H)+: 252.2.

Provenance & Evidence