(+/-)-(4R 5R*)-5-ethoxycarbonyl-1-methyl-4-(4-nitrophenyl)pyrrolidin-2-one → (+/-)-(4R*,5R)-5-ethoxycarbonyl-1-methyl-4-(4-aminophenyl)pyrrolidin-2-one

HRID 1837973Notes

Reaction equation

HRID 1837973 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[N:10]([CH3:11])[C:9](=[O:12])[CH2:8][C@@H:7]1[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1)=[O:5])[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4]([C@@H:6]1[N:10]([CH3:11])[C:9](=[O:12])[CH2:8][C@@H:7]1[C:13]1[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 59066496(+/-)-(4R 5R*)-5-ethoxycarbonyl-1-methyl-4-(4-nitrophenyl)pyrrolidin-2-one

Product 1

HCID 59066479(+/-)-(4R*,5R)-5-ethoxycarbonyl-1-methyl-4-(4-aminophenyl)pyrrolidin-2-oneYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (±)-(4R*,5R*)-5-ethoxycarbonyl-1-methyl-4-(4-nitrophenyl)pyrrolidin-2-one (2.00 g, 6.85 mmol) in EtOAc (15 mL) was added to an argon flushed flask containing 10% palladium on carbon (160 mg). The resulting mixture was placed under an atmosphere of H2 and stirred for 18 h. The reaction mixture then was filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure to give (±)-(4R*,5R*)-5-ethoxycarbonyl-1-methyl-4-(4-aminophenyl)pyrrolidin-2-one (1.66 g, 92%) as a pale oil: TLC (EtOAc) Rf0.48; HPLC ES-MS m/z (rel abundance) 263 (MH+, 100%).

Workup

  1. filtrationThe reaction mixture then was filtered through a pad of Celite®
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-677934c2bcd74aa58aecb04fdab74c10
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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