n-[(3r)-1-(4-Chlorophenyl)-2-oxopyrrolidin-3-yl](phenylmethoxy)carboxamide → (3R)-3-amino-1-(4-chlorophenyl)pyrrolidin-2-one

HRID 855593Notes

Reaction equation

HRID 855593 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][C@@H:10]([NH:13]C(OCC3C=CC=CC=3)=O)[C:9]2=[O:24])=[CH:4][CH:3]=1>C(O)C.C1CCCCC=1.[OH-].[Pd+2].[OH-]>[NH2:13][C@@H:10]1[CH2:11][CH2:12][N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]1=[O:24]

Participants

5

Reactant 1

HCID 21060625n-[(3r)-1-(4-Chlorophenyl)-2-oxopyrrolidin-3-yl](phenylmethoxy)carboxamide

Product 1

HCID 58714338(3R)-3-amino-1-(4-chlorophenyl)pyrrolidin-2-one

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8079CyclohexeneSolvent

Procedure

To a solution of N-[(3R)-1-(4-chlorophenyl)-2-oxopyrrolidin-3-yl](phenylmethoxy)carboxamide (0.2 g, 0.58 mmol) in ethanol (10 ml) and cyclohexene (4 ml) was added palladium hydroxide (40 mg). The reaction was refluxed vigorously overnight. Palladium was removed by filtration and the filtrate was concentrated to yield (3R)-3-amino-1-(4-chlorophenyl)pyrrolidin-2-one.

Workup

  1. temperatureThe reaction was refluxed vigorously overnight
  2. customPalladium was removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0a684f1cf84a4e88a54813af546225ac
Source dataset
uspto-grants-2007_08
Patent number
US07262198B2

Reaction notes

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