Carbon Dioxide → 1-Benzyl-2-oxopyrrolidine-3-carboxylic acid

HRID 1682003Notes

Reaction equation

HRID 1682003 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH2:13]([N:20]1[CH2:24][CH2:23][CH2:22][C:21]1=[O:25])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:26](=[O:28])=[O:27]>CCCCCC.CCOCC>[CH2:13]([N:20]1[CH2:24][CH2:23][CH:22]([C:26]([OH:28])=[O:27])[C:21]1=[O:25])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 7912DiisopropylamineHCID 791761-Benzyl-3-pyrrolidoneHCID 178418339Butyllithium

Product 1

HCID 225602101-Benzyl-2-oxopyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

At -60° C., 150 ml of 1.6 molar butyl lithium solution in n-hexane are added to 28.3 g =39.3 ml (0.28 mol) of diisopropylamine in 400 ml of absolute ether, with stirring and under nitrogen. 35.1 g (0.2 mol) of N-benzyl-2-pyrrolidone dissolved in 150 ml of absolute ether are added dropwize thereto at -60° C. The cooling bath is taken away and dry carbon dioxide is introduced for 15 minutes. After stirring for 10 minutes the mixture is poured onto ice, the organic phase is separated off and extracted twice with 2 molar sodium hydroxide solution. The combined aqueous phases are extracted once with ether and then acidified with concentrated hydrochloric acid, with cooling. The aqueous phase is extracted twice with methylene chloride and, after the organic phase has been dried over magnesium sulphate, it is concentrated by evaporation in vacuo. Yield: 35 g (79.8% of theory), Rf value: 0.42 (silica gel, eluant: 5% ethanol in methylene chloride).

Workup

  1. additionare added dropwize
  2. customat -60° C
  3. stirringAfter stirring for 10 minutes the mixture
  4. additionis poured onto ice
  5. customthe organic phase is separated off
  6. extractionextracted twice with 2 molar sodium hydroxide solution
  7. extractionThe combined aqueous phases are extracted once with ether
  8. temperaturewith cooling
  9. extractionThe aqueous phase is extracted twice with methylene chloride
  10. dry with materialafter the organic phase has been dried over magnesium sulphate, it
  11. concentrationis concentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-3c018565e27e489690c93536cda34ca0
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

Loading…