Acetic Acid → 1-Benzyl-4-ethoxycarbonyl-4-methyl-3-pyrrolidone

HRID 358906Notes

Reaction equation

HRID 358906 reaction equation
C([O:3][C:4]([CH2:6][N:7]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:8][CH:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:10])=O)C.CC(C)([O-])C.[K+].C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:16]([N:7]1[CH2:8][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])([CH3:10])[C:4](=[O:3])[CH2:6]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 13933137N-ethoxycarbonylmethyl-N-(2-ethoxycarbonylpropyl)benzylamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 200671441-Benzyl-4-ethoxycarbonyl-4-methyl-3-pyrrolidoneYield 93.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

60.2 g (0.196 mole) of N-ethoxycarbonylmethyl-N-(2-ethoxycarbonylpropyl)benzylamine [prepared as described in Step (2) above] were added dropwise to a suspension of 24.2 g (0.22 mole) of potassium t-butoxide in 300 ml of toluene over a period of 3 hours, whilst keeping the temperature below 6° C. The mixture was then stirred at the same temperature for 3 hours, after which 13 g of acetic acid were added to it. The toluene layer was separated, washed with water and dried, and the solvent was removed by evaporation under reduced pressure, to give 48.0 g of 1-benzyl-4-ethoxycarbonyl-4-methyl-3-pyrrolidone as a red oil.

Workup

  1. customthe temperature below 6° C
  2. customThe toluene layer was separated
  3. washwashed with water
  4. customdried
  5. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-1eaffd5bdbd542a5b17eac6d799d741a
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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