Acetic Acid → HCID 19738107, compound

HRID 2255423Notes

Reaction equation

HRID 2255423 reaction equation
[CH3:1][CH:2]1[CH:7]2[CH:8]([CH:10]([CH3:12])[CH3:11])[CH2:9][CH:4]([CH:5]([C:13]([O:15]CC)=[O:14])[CH2:6]2)[N:3]1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O)C.[OH-].[Na+].C(O)(=O)C>O>[CH3:1][CH:2]1[CH:7]2[CH:8]([CH:10]([CH3:11])[CH3:12])[CH2:9][CH:4]([CH:5]([C:13]([OH:15])=[O:14])[CH2:6]2)[N:3]1[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 9949378HCID 9949378, compound

Product 1

HCID 19738107HCID 19738107, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 3-methyl-8-isopropyl-2-(phenylmethyl)-2-azabicyclo[2.2.2]octane-6-carboxylate (32.9 g, 100 mmol), ethanol (150 mL), water (150 mL) and NaOH (4.8 g, 120 mmol) were refluxed for 18 hours. The solvent was removed in vacuo and the residue was diluted with water and washed with ether (1×50 mL). The aqueous layer was acidified with acetic acid (6.9 mL, 120 mmol) and extracted with CH2Cl2 (3×50 mL). The organic layers were combined, washed with brine, dried over MgSO4 and concentrated in vacuo to afford 30.3 g (100%) of 3-methyl-8-isopropyl-2-(phenylmethyl)-2-azabicyclo[2.2.2]octane-6-carboxylic acid.

Workup

  1. temperaturewere refluxed for 18 hours
  2. customThe solvent was removed in vacuo
  3. additionthe residue was diluted with water
  4. washwashed with ether (1×50 mL)
  5. extractionextracted with CH2Cl2 (3×50 mL)
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c662a3caa8541ad9cbea2de670a5f09
Source dataset
uspto-grants-1993_08
Patent number
US05240935

Reaction notes

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