Benzyl Alcohol → HCID 67491122, compound

Participants

Reaction Steps

Triethylamine (1.8 mL, 12.9 mmol) and diphenylphosphoryl azide (2.0 mL, 9.27 mmol) were added to a stirred solution of cis-3-[(tert-butoxycarbonyl)amino]cyclohexanecarboxylic acid (2.0 g, 8.22 mmol) in toluene (50 mL), and the resulting mixture was stirred at rt for 3 h. Benzyl alcohol (1.70 mL, 16.4 mmol) was added, and the mixture was heated to 100° C. After 12 h, the reaction mixture was cooled to rt, diluted with EtOAc, and the resulting mixture was washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 0-30% EtOAc/hexanes as eluent) to afford the title compound i-1a. m/z (ES) 371 (M+Na)+

Provenance & Evidence