Benzyl Alcohol → HCID 21054729, compound

Participants

Reaction Conditions

Reaction Steps

Diphenylphosphoryl azide (1.1 equiv.) is added to a solution of 1-(tert-butoxycarbonyl)-4-(trifluoromethyl)piperidine-4-carboxylic acid (3c) (1 equiv.) and Et3N (1 equiv.) in dry toluene at room temperature, and the reaction is warmed gradually to 80° C. The reaction is kept at 80° C. until gas evolution stops, then dry benzyl alcohol (2 equiv.) is added. The reaction is stirred at 80° C. until the isocyanate is consumed, then the solvents are removed in vacuo. The residue is taken up in CH2Cl2 and the solution is washed sequentially with dilute HCl, dilute NaOH, and H2O. The solution is dried (MgSO4) and concentrated in vacuo, and the residue is purified by flash chromatography on silica gel to afford the title compound.

Provenance & Evidence