Methanol → Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylate

HRID 548637Notes

Reaction equation

HRID 548637 reaction equation
S(=O)(=O)(O)O.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[CH2:16][CH:15]([C:19]([OH:21])=[O:20])[CH2:14]2)=[CH:9][CH:8]=1.[CH3:22]O>>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17](=[O:18])[CH2:16][CH:15]([C:19]([O:21][CH3:22])=[O:20])[CH2:14]2)=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 31453971-(4-Hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 2883518Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylateYield 89%

Procedure

A catalytic amount of concentrated sulfuric acid is added to a solution of 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid a50 (3.7 g, 16.7 mmol, 1 eq) in methanol (100 ml) and the mixture is heated at reflux overnight. The solvent is then removed under vacuum, and the residue is dissolved into ethyl acetate. The organic layer is washed with a saturated solution of aqueous sodium hydrogenocarbonate, dried over magnesium sulfate and concentrated under vacuum to afford 3.5 g of methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylate a51.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight
  3. customThe solvent is then removed under vacuum
  4. dissolutionthe residue is dissolved into ethyl acetate
  5. washThe organic layer is washed with a saturated solution of aqueous sodium hydrogenocarbonate
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4a25773aa96847629763a960a81eeaa2
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

Loading…