(R)-N-[1-(4-Nitrophenyl)pyrrolidin-3-yl]acetamide → N-[(3R)-1-(4-aminophenyl)pyrrolidin-3-yl]acetamide

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Reaction Steps

N-[(3R)-1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide (Method 42; 4.5 g, 18 mmol) hydrogenated over 10% palladium/carbon at room temperature and 1 atmosphere pressure in absolute alcohol (200 ml). After filtration of the catalyst and evaporation at reduced pressure gave N-[(3R)-1-(4-aminophenyl)pyrrolidin-3-yl]acetamide as a red oil (3.75 g, 95%). NMR (CDCl3): 1.97 (s, 3H), 1.89-2.03 (m, 1H), 2.22-2.34 (m, 1H), 2.54 (s, 2H), 3.06-3.27 (m, 2H), 3.34-3.48 (m, 2H), 4.52-4.68 (m, 1H), 5.79 (brs, 1H), 6.48 (d, 2H), 6.69 (d, 2H); m/z 220. Treatment with 4M hydrogen chloride in 1,4-dioxane gave the title compound (4.21 g, 96%). LCMS: m/z 220.

Provenance & Evidence