Benzyl Alcohol → Methyl 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate

Participants

Reaction Steps

A mixture of 5-(methoxycarbonyl)bicyclo[3.3.1]nonane-1-carboxylic acid (5.23 g, 24.7 mmol), diphenylphosphonic azide (8.0 mL, 36.9 mmol) and triethylamine (1.0 mL, 136 mmol) in toluene (150 mL) was stirred at room temperature for one hour, and then refluxed for three hours. Benzyl alcohol (4.0 mL, 38.7 mmol) was added, and the mixture was continued to reflux overnight. After cooled to room temperature, the reaction mixture was diluted with ethyl acetate (100 mL), washed with Sat. NaHCO3 and brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate: 20/1) to afford 10 g of methyl 5-(benzyloxycarbonylamino)bicyclo-[3.2.1]octane-1-carboxylate (containing BnOH) as a brown oil. ESI-MS m/z: 318 (M+H)+. It was used in the next step without purification.

Provenance & Evidence