Benzyl Alcohol → 3-Benzyloxycarbonylamino-3-(1-methylallyl)piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

To a solution of an optically-active compound of 3-(1-methylallyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (1.02 g) and triethylamine (967 μl) in toluene (10 ml) heated to 90° C. was added dropwise diphenylphosphoryl azide (1.1 ml). The reaction mixture was stirred at the same temperature for 1 hour, and then thereto were added benzyl alcohol (718 μl) and 4-dimethylaminopyridine (127 mg). The mixture was stirred with refluxing overnight, then cooled to room temperature, and thereto were added water and ethyl acetate. The separated aqueous layer was extracted with ethyl acetate twice, and the combined organic layer was washed with water twice and saturated aqueous sodium chloride solution once, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/acetone=50/1). The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1 to 4/1) to give the titled compound (845 mg).

Provenance & Evidence