Benzyl Alcohol → tert-Butyl 4-{[(benzyloxy)carbonyl]amino}-4-methylpiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 1-{[(1,1-dimethylethyl)oxy]carbonyl}-4-methyl-4-piperidinecarboxylic acid (12.092 g, 49.7 mmol) in toluene (300 ml) was treated with triethylamine (13.85 ml, 99 mmol) and then diphenylphosphoryl azide (21.42 ml, 99 mmol), heated to 90° C. for 2 h (bubbling observed) before treatment with benzyl alcohol (10.34 ml, 99 mmol). The reaction was then heated at 90° C. for a further 18 h, then cooled, treated with saturated aqueous sodium bicarbonate (500 ml), the organic extracts were separated and the aqueous extracted with diethyl ether (200 ml), the combined organic extracts were dried (MgSO4), filtered, evaporated, columned (0-50% ethyl acetate:40-60 petroleum ether, Rf=0.4 in 4:1 ethyl acetate:40-60 petroleum ether) to give product as a clear oil (15.473 g, 89%).

Provenance & Evidence