Trifluoroacetic acid → rac-(3R,4S)-1-Benzyl-3-(4-fluoro-phenyl)-4-nitro-pyrrolidine

Participants

Reaction Conditions

Reaction Steps

A solution of N-(methoxymethyl)-N-(phenylmethyl)-N-(trimethylsilyl)methylamine (8.00 g, 33.6 mmol) in CH2Cl2 (140 ml) was added drop wise, over a 30 minutes period, to a stirred solution of 1-fluoro-4-((E)-2-nitro-vinyl)-benzene (5.12 g, 30.6 mmol) and trifluoroacetic acid (0.23 ml, 3.1 mmol) in CH2Cl2 (200 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 6.60 g (72%) of the title compound as a light yellow oil.

Provenance & Evidence