Trifluoroacetic acid → (3SR,4RS)-1-benzyl-3-(4-chloro-phenyl)-4-nitro-pyrrolidine

Participants

Reaction Conditions

Reaction Steps

A solution of N-(methoxymethyl)-N-(phenylmethyl)-N-(trimethylsilyl)methylamine (6.70 g, 28.2 mmol) in CH2Cl2 (100 ml) was added drop wise, over a 30 minutes period, to a stirred solution of 1-chloro-4-((E)-2-nitro-vinyl)-benzene (4.97 g, 27.1 mmol) and trifluoroacetic acid (0.31 g, 2.7 mmol) in CH2Cl2 (150 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/H 1:4) afforded 6.75 g (79%) of the title compound as a colorless oil.

Provenance & Evidence