Hydrochloric Acid → Ethyl 1-benzyl-4-oxopyrrolidine-3-carboxylate

HRID 2112749Notes

Reaction equation

HRID 2112749 reaction equation
[CH2:1]([N:8]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:9][C:10](OCC)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Cl.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:9][C:10](=[O:11])[CH:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69929Ethyl N-(2-ethoxy-2-oxoethyl)-N-(phenylmethyl)-beta-alaninateHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 274831Ethyl 1-benzyl-4-oxopyrrolidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Above-prepared ethyl 3-[N-benzyl-N-(ethoxycarbonylmethyl)amino]propionate (14.0 g, 0.0479 mol) was dissolved in toluene (100 mL), and the solution was mixed with potassium tert-butoxide (5.9 g, 0.0525 mol) gradually added under ice-cooling, followed by stirring under ice-cooling for two hours. The reaction mixture was mixed with diluted hydrochloric acid (about 1 mol/L, 100 mL) under ice-cooling, followed by shaking and separation, to yield an aqueous layer. Saturated aqueous sodium bicarbonate solution (300 mL) was added dropwise to the aqueous layer, and ethyl acetate (400 mL) was further added thereto, followed by shaking and separation. After drying the organic layer over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, to thereby yield ethyl 1-benzyl-4-oxopyrrolidine-3-carboxylate (9.23 g, in a yield of 78%).

Workup

  1. additiongradually added under ice-
  2. temperaturecooling
  3. temperaturecooling for two hours
  4. temperaturecooling
  5. stirringby shaking
  6. customseparation
  7. customto yield an aqueous layer
  8. additionwas further added
  9. stirringby shaking
  10. customseparation
  11. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate
  12. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e5019015abc44035a336215f048d3903
Source dataset
uspto-grants-2009_04
Patent number
US07524852B2

Reaction notes

Loading…