2-[4-(Benzyloxy)-2-oxo-2,5-dihydro-1H-pyrrol-1-yl]acetamide → Oxiracetam

HRID 1905547Notes

Reaction equation

HRID 1905547 reaction equation
C([O:8][C:9]1[CH2:13][N:12]([CH2:14][C:15]([NH2:17])=[O:16])[C:11](=[O:18])[CH:10]=1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd].[Pt]=O>[OH:8][CH:9]1[CH2:13][N:12]([CH2:14][C:15]([NH2:17])=[O:16])[C:11](=[O:18])[CH2:10]1

Participants

6

Reactant 2

HCID 142744722-[4-(Benzyloxy)-2-oxo-2,5-dihydro-1H-pyrrol-1-yl]acetamide2×HCID 178418361HCID 178418361, compound

Product 1

HCID 4626Oxiracetam

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

Catalytic hydrogenolysis and hydrogenation of 4-benzyloxy-3-pyrrolin-2-on-1-yl acetamide 3.00 g of 4-benzyloxy-3-pyrrolin-2-on-1-yl acetamide was dissolved in 30 ml of concentrated acetic acid and mixed with 240 mg of palladium 5 percent on activated carbon and 24 mg of platinum oxide. Hydrogenolysis and hydrogenation at 15 bars of hydrogen pressure and room temperature were performed for 65 hours. Then filtering off from the catalyst and evaporation of the solvent were performed. The residue was picked up in H2O and allowed to run over 5.0 g of weakly basic ion exchanger. The water was distilled off and the residue mixed with 10 ml of acetone. 1.53 g of nearly white 4-hydroxypyrrolidin-2-on-1-yl acetamide with a melting point of 163.5° to 165.7° C. was obtained.

Workup

  1. filtrationThen filtering off from the catalyst and evaporation of the solvent
  2. distillationThe water was distilled off
  3. additionthe residue mixed with 10 ml of acetone

Sources & evidence

ORD record
ord-1ec0859131be4dbbb5b33508ae58bf95
Source dataset
uspto-grants-1989_06
Patent number
US04843166

Reaction notes

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