Ethanol → Trans-4-(2-oxo-pyrrolidin-1-yl)cyclohexanecarboxylic acid

HRID 2116765Notes

Reaction equation

HRID 2116765 reaction equation
[N:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([C:13]([O:15]CC)=[O:14])[CH2:9][CH2:8]2)[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].C(O)C.[O-]CC.[Na+]>O>[N:1]1([CH:7]2[CH2:8][CH2:9][CH:10]([C:13]([OH:15])=[O:14])[CH2:11][CH2:12]2)[CH2:5][CH2:4][CH2:3][C:2]1=[O:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 23115699Ethyl 4-(2-oxopyrrolidin-1-yl)cyclohexane-1-carboxylate

Product 1

HCID 11572026Trans-4-(2-oxo-pyrrolidin-1-yl)cyclohexanecarboxylic acidYield 65.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To ethyl 4-(2-pyrrolidon-1-yl)cyclohexylcarboxylate (5.0 g, mixture of cis and trans isomers, cis:trans=61:39) are added ethanol (25.0 mL, 5V/W) and sodium ethoxide (2.0 equiv. 0.0132 mol), and the mixture is stirred at room temperature for 20 hours. After adding water (5.0 mL, 1V/W), the reaction solution is stirred at room temperature for 2 hours, and evaporated to remove ethanol under reduced pressure. The residue is acidified by adding 2 N hydrochloric acid, and thereto is added an excessive amount of crystalline sodium chloride followed by extraction with methylene chloride. The extract is dried, and evaporated to remove the solvent under reduced pressure. The resulting crystals are collected with toluene to give 4-(2-pyrrolidon-1-yl)cyclohexylcarboxylic acid (2.9 g, trans:cis=88:12, yield 58%).

Workup

  1. stirringthe reaction solution is stirred at room temperature for 2 hours
  2. customevaporated
  3. customto remove ethanol under reduced pressure
  4. additionby adding 2 N hydrochloric acid
  5. additionis added an excessive amount of crystalline sodium chloride
  6. extractionfollowed by extraction with methylene chloride
  7. customThe extract is dried
  8. customevaporated
  9. customto remove the solvent under reduced pressure
  10. customThe resulting crystals are collected with toluene

Sources & evidence

ORD record
ord-7cce948c4a5e4f10a8e5d9efebc2897b
Source dataset
uspto-grants-2008_10
Patent number
US07439368B2

Reaction notes

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