1-Naphthalenemethanamine → HCID 86587437, compound

Participants

Reaction Steps

A solution of 3-[(tert-butoxy)carbonylamino]benzoic acid (250 mg, 1.05 mmol), 1-naphthylmethylamine (170 mg, 1.05 mmol), diethyl cyanophosphonate (260 mg, 1.6 mmol), and triethylamine (0.22 ml, 1.6 mmol) in acetonitrile was stirred overnight. The solvent was evaporated, and the residue was partitioned between ethyl acetate and 1N HCl. The layers were separated, and the organic phase was washed twice more with 1N HCl, then 3 times each with water and brine. The solvent was removed in vacuo, and the crude product was purified on a silica gel column, eluting with 20% ethyl acetate in hexane, to deliver 270 mg of the amide.

Provenance & Evidence