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

HRID 271252Notes

Reaction equation

HRID 271252 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-9704df48e6c64055b65f54956a2424ab
Source dataset
uspto-grants-2008_11
Patent number
US07452889B2

Reaction notes

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