1-(4-Chlorophenyl)-2,5-bis(4-nitrophenyl)pyrrolidine → 4,4'-(trans-1-(4-Chlorophenyl)pyrrolidine-2,5-diyl)dianiline

Participants

Reaction Steps

To a solution of the product of example 85A (0.214 g, 0.505 mmol) in EtOH (2.52 mL) and THF (2.52 mL) was added platinum(IV) oxide (0.115 g, 0.505 mmol), and the resulting mixture was stirred at rt under 1 atm H2 overnight. The mixture was filtered through celite, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-12% EtOAc in hexane to give a mixture of the title compound and some dechlorinated product (4,4′-(trans-1-phenylpyrrolidine-2,5-diyl)dianiline).

Provenance & Evidence