Trifluoroacetic acid → Ethyl 1-benzyl-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of N-(methoxymethyl)-N-(phenylmethyl)-N-(trimethylsilyl)methylamine (2.46 g, 10.4 mmol) in CH2Cl2 (15 mL) was added dropwise, over a 30 minutes period, to a stirred solution of (E)-3-(3,4-dichloro-phenyl)-acrylic acid ethyl ester (2.40 g, 10.4 mmol) and trifluoroacetic acid (0.08 mL, 1 mmol) in CH2Cl2 (10 mL) at 0° C. The ice bath was removed and the solution was stirred at 25° C. for an additional 48 h. It was then concentrated and purification by flash chromatography (SiO2, EtOAc/heptane 1:4) afforded 2.48 g (66%) of the title compound as a yellow oil. ES-MS m/e: 379.3 (M+H+).

Provenance & Evidence