Ammonia → benzyl N-(2-cyanopropan-2-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

Acetone cyanohydrin (17 grams, 200 mmol) was added to 400 mL of a 2M solution of NH3 in methanol and the resulting mixture stirred under N2 for 4 days. The solvent was removed in vacuo and the remaining residue dissolved in 250 mL of H2O. After cooling to 10° C., the solution was treated with Na2CO3 (21 grams, 200 mmol) and 95% benzyloxy chloroformate (33 mL, 230 mmol) and stirring continued overnight. Ethyl acetate was added and the mixture transferred to a seperatory funnel. The aqueous layer was removed and the ethyl acetate solution washed with saturated NaHCO3. After drying over Na2SO4 the solvent was removed to yield a solid which was triturated with hexanes to provide the title compound.

Provenance & Evidence