Ethanol → HCID 21254110, compound

HRID 1531563Notes

Reaction equation

HRID 1531563 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][C:5]([CH3:17])([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[C:4]1=[O:18])[CH3:2].C(O)C.[H][H]>[Pd].CCCCCC.CCOC(C)=O>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2([CH3:17])[CH2:6][CH2:7][N:3]([CH2:1][CH3:2])[C:4]2=[O:18])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 21254079HCID 21254079, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21254110HCID 21254110, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 770 mg (3.1 mmol) (±)-1-ethyl-3-methyl-3-(4-nitrophenyl)pyrrolidin-2-one, 50 mg of 10% palladium on carbon, and 50 mL of absolute ethanol was shaken with hydrogen (initial hydrogen pressure 46 psig) in a pressure vessel for 2.5 hours. The catalyst was removed by filtration through Celite under nitrogen, and the filter cake was washed with additional ethanol. Concentration of the filtrate in vacuo gave 684 mg (quantitative) of an extremely pale pink oil; essentially homogeneous by TLC in 1:1 hexane-EtOAc. 500 MHz 1H NMR (CDCl3) was consistent with the assigned structure. Mass spectrum (PB-NH3/CI): m/e=219.1 (M+H).

Workup

  1. customThe catalyst was removed by filtration through Celite under nitrogen
  2. washthe filter cake was washed with additional ethanol
  3. customConcentration of the filtrate in vacuo gave 684 mg (quantitative) of an extremely pale pink oil

Sources & evidence

ORD record
ord-62d5afa631c84f3e83506603db345df0
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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