Triphenylphosphine → N,O-bisphenyloxycarbonyl-t-butyloxycarbonylamino-2-propylhydroxylamine

Participants

Reaction Conditions

Reaction Steps

A one liter roundbottom flask was charged with N-Boc-1-amino-2-propanol (26.42 g, 0.0151 mol), triphenylphosphine (41.4 g, 0.158 mol), and N,O-bisphenyloxycarbonylhydroxylamine (43.2 g, 0.158 mol), and dry THF (550 mL). The solution was cooled to 0° C., and diethylazodicarboxylate (24.9 mL, 0.158 mol) was added in THF (50 mL). The reaction was stirred one hour after removing the cooling bath, and concentrated under vacuum. Chromatographic purification is enhanced by adding dichloromethane (200 mL) and concentrating in vacuo twice to remove THF before column chromatography (400 g silica gel, 15% EtOAc/Hex) to provide N,O-bisphenyloxycarbonyl-t-butyloxycarbonylamino-2-propylhydroxylamine (54.4 g, 80%).

Provenance & Evidence