Acetic Acid → (-)-Norcocaine

HRID 1898784Notes

Reaction equation

HRID 1898784 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 56.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Cocaine (1.0 g, 3.29 mmol) was dissolve in a mixed solvent of acetonitrile (55 ml) and water (110 ml). Acetic acid (1 ml) was added to the mixture to form a weak acidic solution. To this solution was added an aqueous solution (42 ml) of potassium permanganate (1.06 g, 7.55 mmol) dropwise over 8 h. After the addition, the mixture was stirred overnight at room temperature. The resulting precipitate was removed by filtration, and potassium carbonate was added to the filtrate to form a basic solution. The solution was extracted with diethyl ether three times, and anhydrous potassium sulfate was added to the organic layer for dryness. The ether was distilled off under reduced pressure. The product was purified by silica gel thin-layer chromatography (eluent: ammonia-saturated chloroform) to form norcocaine (536 mg, MW=289.4, Yield: 56%).

Workup

  1. customto form a weak acidic solution
  2. additionAfter the addition
  3. customThe resulting precipitate was removed by filtration, and potassium carbonate
  4. additionwas added to the filtrate
  5. customto form a basic solution
  6. extractionThe solution was extracted with diethyl ether three times, and anhydrous potassium sulfate
  7. additionwas added to the organic layer for dryness
  8. distillationThe ether was distilled off under reduced pressure
  9. customThe product was purified by silica gel thin-layer chromatography (eluent: ammonia-saturated chloroform)

Sources & evidence

ORD record
ord-74cca9d9a7604c058e178a67f7bde52c
Source dataset
uspto-grants-1996_11
Patent number
US05571727

Reaction notes

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