Benzyl Alcohol → HCID 178453647, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of trans-4-(tert-butoxycarbonylamino-methyl)-cyclohexanecarboxylic acid (46.9 g, 0.18 mol) in benzene (300 mL) were added triethylamine (24.2 g, 0.24 mol) and diphenylphosphoryl azide (55.9 g, 0.20 mol). The reaction mixture was stirred at 80° C. for 1 hr. To the mixture was added benzyl alcohol (25.9 g, 0.24 mol) and stirred at 100° C. for 4 hr. The mixture was subsequently cooled to ambient temperature for overnight, concentrated, and the resulting pale orange solid dissolved in EtOAc. The organic layer was washed with water (three times), concentrated, and the residue was purified by column chromatography (silica gel, 50% EtOAc in hexane) to give trans-[4-(tert-butoxycarbonylamino-methyl)-cyclohexyl]-carbamic acid benzyl ester (66.7 g, 100%) as a white solid.

Provenance & Evidence