N-(2-phenylethyl)acetamide → Methyl alpha,alpha-dimethyl-beta-oxo-beta-[4-(2-acetamidoethyl)-phenyl]-propionate

Participants

Reaction Steps

The ethyl α,α-dimethyl-β-[4-(2-aminoethyl)-phenyl]-propionate hydrochloride (m.p. 113°-117° C.) used as starting material is prepared in the following manner: N-acetylphenethylamine is reacted with dimethylmalonic acid methyl ester chloride according to Friedel-Crafts method to give methyl α,α-dimethyl-β-oxo-β-[4-(2-acetamidoethyl)-phenyl]-propionate (b.p. 215°-220° C./0.1 mm.Hg.), this then reduced, via methyl α,α-dimethyl-β-hydroxy-β-[4-(2-acetamidoethyl)-phenyl]-propionate (m.p. 120°-123° C.) to give methyl α,α-dimethyl-β-[4-(2-acetamidoethyl)-phenyl]-propionate (b.p. 180°-190° C./0.1 mm Hg.), saponified to give α,α-dimethyl-β-[4-(2-aminoethyl)-phenyl]-propionic acid hydrochloride (m.p. 230°-235° C.) and thereafter esterified to give the desired ethyl ester hydrochloride.

Provenance & Evidence