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

HRID 1441367Notes

Reaction equation

HRID 1441367 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][C:16](=[O:18])[CH3:17])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][C:16](=[O:18])[CH3:17])[CH2:11]2)=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 67147876(R)-N-[1-(4-Nitrophenyl)pyrrolidin-3-yl]acetamide

Product 1

HCID 68687001N-[(3R)-1-(4-aminophenyl)pyrrolidin-3-yl]acetamideYield 95%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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.

Workup

  1. filtrationAfter filtration of the catalyst and evaporation at reduced pressure

Sources & evidence

ORD record
ord-9c6f76ed7deb41a7a0289dc9229af12a
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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