Acetic Acid → (-)-Norcocaine

HRID 566175Notes

Reaction equation

HRID 566175 reaction equation
C[N:2]1[C@H:6]2[C@@H:7]([C:19]([O:21][CH3:22])=[O:20])[C@@H:8]([O:10][C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:12])[CH2:9][C@@H:3]1[CH2:4][CH2:5]2.C(O)(=O)C.[Mn]([O-])(=O)(=O)=O.[K+]>C(#N)C.O>[CH3:22][O:21][C:19]([C@H:7]1[C@@H:8]([O:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])[CH2:9][C@H:3]2[NH:2][C@@H:6]1[CH2:5][CH2:4]2)=[O:20]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 446220CocaineHCID 516875Potassium Permanganate

Product 1

HCID 644007(-)-NorcocaineYield 56.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Cocaine (500 mg) was dissolved in a mixture (21 ml) of acetonitrile and water (1:2). Acetic acid (0.5 ml) was added to the solution to adjust its pH to approximately 5. To the solution was added dropwise 21 ml aqueous potassium permanganate (KMnO4=534 mg, 3.78 mmol, 2.05 eq.) over 3 hours. The solution was stirred overnight at room temperature. After removing the resulting precipitate by filtration, potassium carbonate (1050 mg) was added to the filtrate to adjust its pH to approximately 8. The filtrate was extracted with ether three times and dried over anhydrous sodium sulfate overnight. The sodium sulfate was removed out of the extract and ether was distilled off under reduced pressure to give colorless liquid. The liquid was purified by silica-gel thin layer chromatography (hereinafter abbreviated as TLC) using as an eluent ammonia saturated chloroform to give norcocaine (269 mg) of Formula (4):

Workup

  1. customAfter removing the resulting precipitate
  2. filtrationby filtration, potassium carbonate (1050 mg)
  3. additionwas added to the filtrate
  4. extractionThe filtrate was extracted with ether three times
  5. dry with materialdried over anhydrous sodium sulfate overnight
  6. customThe sodium sulfate was removed out of the
  7. extractionextract
  8. distillationether was distilled off under reduced pressure
  9. customto give colorless liquid
  10. customThe liquid was purified by silica-gel thin layer chromatography (

Sources & evidence

ORD record
ord-745f7eb1cd524d5e80a99824cf6d1190
Source dataset
uspto-grants-2001_01
Patent number
US06174723B1

Reaction notes

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