Furfuryl Alcohol → 1-[[(2-Furanylmethoxy)carbonyl]amino]cyclohexanecarboxylic acid methyl ester

Participants

Reaction Steps

3.67 g (30 mmol) of dimethylaminopyridine was added to a solution of 65.48 g (0.3 mol) of di-t-butyl dicarbonate in 300 ml of anhydrous toluene, and the mixture was stirred at room temperature for 15 minutes. A solution of 47.17 g (0.3 mol) of 1-aminocyclohexanecarboxylic acid methyl ester in 100 ml of anhydrous toluene was added to the reaction solution, and the mixture was stirred at room temperature for 1 hour. After 60.71 g (0.6 mol) of triethylamine and 44.1 g (0.45 mol) of furfuryl alcohol were further added thereto, the mixture was heated under reflux for 3 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. The obtained residue was triturated in a mortal and stirred in a mixed solution of 5 ml of hydrochloric acid and 3 liters of water for 18 hours. The obtained crystal was collected by filtration to give 74.37 g (88%) of the title compound.

Provenance & Evidence