Cyanuric chloride → tert-Butyl ((1-(cyanomethyl)cyclohexyl)methyl)carbamate

Participants

Reaction Steps

Cyanuric chloride (39.5 g, 0.214 mol) was added to (1-carbamoylmethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester (3) (116 g, 0.429 mol) in 400 mL DMF. An ice-water bath was used to moderate the exotherm, and the reaction mixture was stirred at room temperature for 1.5 hours. The mixture was poured into ice-water containing 120 g (1.43 mol) NaHCO3 and was extracted 4× EtOAc. The extracts were washed 1× water, 2× brine and dried over Na2SO4. Evaporation yielded an oil which was taken up in 3:1 hexane/EtOAc and filtered through silica gel. Evaporation yielded white crystals (86.5 g, 80%); mp 54–58° C.

Provenance & Evidence