Benzyl Alcohol → HCID 178454052, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of cis-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (50.0 g, 206 mmol) in benzene were added triethylamine (26.9 g, 266 mmol) and phosphorazidic acid diphenyl ester (62.2 g, 226 mmol). The reaction mixture was stirred at 80° C. for 1 hr. Benzyl alcohol (31.4 g, 290 mmol) was added and the mixture was stirred at reflux for 24 hr. The reaction mixture was concentrated and the residue was dissolved in EtOAc and H2O. The organic layer was separated and the aqueous layer was extracted with EtOAc (twice). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by flash chromatography (silica gel, 30% EtOAc in hexane) to give cis-(4-tert-butoxycarbonylamino-cyclohexyl)-carbamic acid benzyl ester (54.1 g, 76%) as a colorless oil.

Provenance & Evidence