HCID 18361947, compound → HCID 18361990, compound

HRID 382798Notes

Reaction equation

HRID 382798 reaction equation
[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH:11]([CH2:18][N+:19]([O-])=O)[CH2:12][C:13](OCC)=[O:14])=[CH:5][C:4]=1[O:22][CH3:23])[CH3:2]>C(O)C>[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH:11]2[CH2:18][NH:19][C:13](=[O:14])[CH2:12]2)=[CH:5][C:4]=1[O:22][CH3:23])[CH3:2]

Participants

3

Reactant 1

HCID 18361947HCID 18361947, compound

Product 1

HCID 18361990HCID 18361990, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15.1 g (46.4 mmol) of ethyl 3-(4-ethyl-3,5-dimethoxy-phenyl)-4-nitro-butanoate dissolved in 300 ml of ethanol were hydrogenated on Raney-nickel while stirring over a period of 2.5 hours. The catalyst was filtered off, washed several times with ethanol and the combined ethanol phases were concentrated in a vacuum to a volume of 200 ml. The reaction mixture was treated with 1.7 g of sodium acetate and 50 mg of p-toluenesulphonic acid and heated under reflux over 24 hours. Subsequently, the mixture was concentrated in a vacuum and the residue was purified by column chromatography on silica gel (methylene chloride/methanol 19:1). 8.85 g (76%) of 4-(4-ethyl-3,5-dimethoxy-phenyl)-pyrrolidin-2-one were obtained as a beige solid with m.p. 156°.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed several times with ethanol
  3. concentrationthe combined ethanol phases were concentrated in a vacuum to a volume of 200 ml
  4. additionThe reaction mixture was treated with 1.7 g of sodium acetate and 50 mg of p-toluenesulphonic acid
  5. temperatureheated
  6. temperatureunder reflux over 24 hours
  7. concentrationSubsequently, the mixture was concentrated in a vacuum
  8. customthe residue was purified by column chromatography on silica gel (methylene chloride/methanol 19:1)

Sources & evidence

ORD record
ord-f8cc78fe13484793a629ee73d785ffef
Source dataset
uspto-grants-2001_10
Patent number
US06310208B1

Reaction notes

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