Ammonium Chloride → 4,4'-(1-(4-Fluorophenyl)pyrrolidine-2,5-diyl)dianiline

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from Example 1D (0.501 g, 1.23 mmol) in ethanol (5 ml) and THF (5.00 ml) was added iron powder (0.412 g, 7.38 mmol) and a solution of ammonium chloride (0.197 g, 3.69 mmol) in water (1.0 ml). The resulting mixture was stirred at 80° C. for 45 min. The mixture was cooled, filtered through celite, washed with ethanol, and concentrated in vacuo. The crude product was purified by chromatography on silica gel using a solvent gradient of 0-100% ethyl acetate in hexanes to give the title compound as a mixture of cis and trans isomers (0.135 gm, 32%).

Provenance & Evidence