Ethyl 4-amino-5-oxo-1-phenyl-3-pyrrolidinecarboxylate → 1-Phenylpyrrolidine-2,3-dione

HRID 1590260Notes

Reaction equation

HRID 1590260 reaction equation
N[CH:2]1[C:6](=[O:7])[N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH:3]1C(OCC)=O.Cl.[OH2:20]>>[C:8]1([N:5]2[CH2:4][CH2:3][C:2](=[O:20])[C:6]2=[O:7])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 19023548Ethyl 4-amino-5-oxo-1-phenyl-3-pyrrolidinecarboxylateHCID 21885828Hydrate;hydrochloride

Product 1

HCID 190235711-Phenylpyrrolidine-2,3-dione

Procedure

According to the procedure of Southwick [J. Org. Chem. 21, 1087 (1956)]the ethyl ester pyrrolidinone of Example S (1.0 g, 4.0 mmol) was suspended in 75 ml of 20% HCl/H2O and refluxed for 3.5 h The reaction was cooled and filtered and the filtrate was extracted with CHCl3 (4×150 ml). Concentration of the combined extracts gave an off-white solid (358 mg). 'NMR(300 MHZ, CDCl3) δ2.92 (t, 2H), 4.17 (t, 2H), 7.32 (t, 1H), 7.98 (t, 2H), 7.84 (d, 2H).

Workup

  1. temperaturerefluxed for 3.5 h The reaction
  2. temperaturewas cooled
  3. filtrationfiltered
  4. extractionthe filtrate was extracted with CHCl3 (4×150 ml)

Sources & evidence

ORD record
ord-85c13e5707fc4453b623d1f56baa9967
Source dataset
uspto-grants-1993_04
Patent number
US05202344

Reaction notes

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