Benzyl Alcohol → tert-Butyl 3-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Diphenylphosphorylazide (2.60 g) was added dropwise to a mixture of N-(tert-butoxycarbonyl)nipecotic acid (2.06 g) and triethylamine (1.00 g) in toluene (20 mL). The reaction mixture was warmed in an oil bath over 10 minutes at 100° C. Stirring was continued for 2 hours at 100° C., then the reaction vessel was taken out from the oil bath. After reflux was ceased, benzyl alcohol (1.07 g) was added to the reaction mixture. The mixture was stirred for 3 hours at 100° C., and then poured into a mixture of 3.6% hydrochloric acid, ice and ethyl acetate. The separated organic layer was washed with brine, an aqueous saturated sodium bicarbonate solution and brine, successively. The resultant was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by a silica gel column chromatography eluting with 30% ethyl acetate in hexane to give 3-(benzyloxycarbonylamino)-1-tert-butoxycarbonylpiperidine (2.66 g) as an oil.

Provenance & Evidence