Hydrochloric Acid → HCID 68978225, compound

HRID 2218567Notes

Reaction equation

HRID 2218567 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[N:12]1[CH2:16][CH:15]([CH3:17])[CH2:14][C:13]1=[O:18])=[O:5])C.[OH-].[Li+].Cl>C1COCC1>[CH3:17][CH:15]1[CH2:16][N:12]([C@@H:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C@H:6]2[C:4]([OH:5])=[O:3])[C:13](=[O:18])[CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68977194HCID 68977194, compound

Product 1

HCID 68978225HCID 68978225, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

trans-2-(4-Methyl-2-oxo-pyrrolidin-1-yl)-cyclohexanecarboxylic acid ethyl ester (395 mg) was dissolved in absolute THF (15 ml) and 1 N lithium hydroxide solution (5.12 ml) was added. The resulting mixture was refluxed over night. The reaction mixture was cooled to room temperature and then HCl conc. (1.80 ml) was added (pH=2). The mixture was evaporated and then diluted with toluene and evaporated to remove the water. The residue was purified by flash chromatography (AcOEt/MeOH 85/15) to give the product as a 1:1 mixture of epimers as light yellow foam (435 mg). MS (ESI): 224.3 (M+H+−).

Workup

  1. temperatureThe resulting mixture was refluxed over night
  2. customThe mixture was evaporated
  3. additiondiluted with toluene
  4. customevaporated
  5. customto remove the water
  6. customThe residue was purified by flash chromatography (AcOEt/MeOH 85/15)
  7. customto give the product

Sources & evidence

ORD record
ord-a6ef475d9f5f4616ad8c250d1767c673
Source dataset
uspto-grants-2008_08
Patent number
US07411093B2

Reaction notes

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