Acetic Acid → (-)-Norcocaine

HRID 650239노트

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HRID 650239 반응식
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]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 446220CocaineHCID 516875Potassium Permanganate

생성물 1

HCID 644007(-)-Norcocaine수율 56.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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):

후처리

  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 (

출처 및 근거

ORD 기록
ord-1f1c858497794fd69ac4c8a456220486
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06271381B1

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