Sodium ethoxide → 4-Oxo-pyrrolidine-1,3-dicarboxylic acid diethyl ester

HRID 659045Notes

Reaction equation

HRID 659045 reaction equation
[CH2:1]([O:3][C:4]([N:6]([CH2:14][C:15]([O:17]CC)=O)[CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])[CH3:2].CC[O-].[Na+]>CCO>[O:17]=[C:15]1[CH2:14][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH:8]1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 4381617ethyl 3-[ethoxycarbonyl-(2-ethoxy-2-oxoethyl)amino]propanoate

Product 1

HCID 2763144-Oxo-pyrrolidine-1,3-dicarboxylic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Intermediate (e) (18.0 g, 65.2 mmol) was added to an ice bath cooled solution of NaOEt (32.6 mL) (21% by weight in EtOH) in absolute EtOH (41.7 mL) under a nitrogen atmosphere. The ice bath was removed and the mixture was heated at 80° C. for about 12 h until the condensation was complete as observed by TLC. The mixture was poured onto ice/water and extracted into EtOAc. The solvent was dried with Na2SO4, filtered, and evaporated to afford crude intermediate (f) as an off white solid (14.05 g) which was carried on without purification.

Workup

  1. customThe ice bath was removed
  2. additionThe mixture was poured onto ice/water
  3. extractionextracted into EtOAc
  4. dry with materialThe solvent was dried with Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-cdf601ddefbc45f5a832363300a87067
Source dataset
uspto-grants-2011_12
Patent number
US08080556B2

Reaction notes

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