4-Fluoroaniline → 1-(4-Fluorophenyl)-2,5-bis(4-nitrophenyl)pyrrolidine

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Reaction Conditions

Reaction Steps

The product from Example 1C (0.6 gm, 1.228 mmol) and 4-fluoroaniline (2.0 ml, 20.82 mmol) were combined and stirred at 50° C. overnight. The resulting mixture was partitioned between 0.2 N HCl (50 ml) and ethyl acetate (3×50 ml), and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica gel using a solvent gradient of 0-40% ethyl acetate in hexane to give the title compound as a mixture of cis and trans isomers (0.5 gm, 100% yield).

Provenance & Evidence