Benzyl Alcohol → HCID 178453647, compound

Participants

Reaction Steps

A solution of trans-4-(tert-butoxycarbonylaminomethyl)cyclohexanecarboxylic acid (19.76 g), diphenylphosphoryl azide (25.36 g) and triethylamine (12 ml) in toluene (210 ml) was stirred at room temperature for 30 minutes and at 100° C. for 30 minutes. Into the reaction mixture was added benzyl alcohol (9.7 ml), and the resulting mixture was heated at reflux for 24 hours. After cooling to room temperature, the reaction mixture was mixed with water and was extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid, water, an aqueous saturated solution of sodium bicarbonate and an aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate. After the resulting organic layer was concentrated under reduced pressure, the residue was subjected to purification using column chromatography (ethyl acetate/hexane 1:2) and to recrystallization (ethyl acetate/hexane) to obtain benzyl trans-4-(tert-butoxycarbonylaminomethyl)cyclohexylcarbamate (18.93 g) as colorless crystals.

Provenance & Evidence