Triethylamine → Ethyl[N-(3-pyridylmethyl)-N-(methoxycarbonylethyl)carbamoyl]acetate

Participants

Reaction Steps

A mixture of methyl 3-(3-pyridylmethylamino)propionate (28.72 g), triethylamine (22 ml) and methylene chloride (240 ml) is cooled to 5°-10° C., and thereto is added dropwise a solution of ethoxycarbonylacetyl chloride (23.38 g) in methylene chloride (60 ml). The mixture is stirred at room temperature for one hour. The mixture is filtered to remove precipitates (triethylamine hydrochloride). The filtrate is washed with water, dried and then distilled to remove the solvent. The residue is purified by silica gel column chromatography (solvent, ethyl acetate) to give ethyl[N-(3-pyridylmethyl)-N-(methoxycarbonylethyl)carbamoyl]acetate (35.22 g, 77.3%) as oil.

Provenance & Evidence