Dimethylformamide → 3-Chloro-2-formyl-8-methyl-8-azabicyclo[3.2.1]oct-2-ene oxalate

HRID 257447

반응식

HRID 257447 반응식
CN(C)[CH:3]=[O:4].P(Cl)(Cl)([Cl:8])=O.[CH3:11][N:12]1[CH:16]2[CH2:17][C:18]([CH2:20][CH:13]1[CH2:14][CH2:15]2)=[O:19].[C:21](=[O:24])([O-:23])[O-:22].[K+].[K+]>>[C:3]([OH:4])(=[O:19])[C:21]([OH:23])=[O:22].[Cl:8][C:18]1[CH2:20][CH:13]2[N:12]([CH3:11])[CH:16]([CH2:15][CH2:14]2)[C:17]=1[CH:21]=[O:24]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 79038Npc164516

생성물 1

HCID 189608383-Chloro-2-formyl-8-methyl-8-azabicyclo[3.2.1]oct-2-ene oxalate

반응 조건

온도
70 °C

실험 절차

To a dimethylformamide (4.5 ml, 60 mmol) at 0° C. was added phosphorous oxychloride (3 ml, 30 mmol). Tropinone (2 g, 13 mmol) was added, and the reaction mixture heated to 70° C. for 1/2 h After cooling, crushed ice was added and then solid potassium carbonate until alkaline reaction. The water solution was extracted with ether (3×30 ml). The ether extracts were dried and evaporated. The crude compound was purified by column chromatography with acetone as eluent. The title compound was precipitated with a 1M oxalic acid acetone solution, filtered and dried. M.p. 136°-137° C. decomposes.

후처리

  1. temperatureAfter cooling
  2. customcrushed ice
  3. additionwas added
  4. extractionThe water solution was extracted with ether (3×30 ml)
  5. dry with materialThe ether extracts were dried
  6. customevaporated
  7. customThe crude compound was purified by column chromatography with acetone as eluent
  8. customThe title compound was precipitated with a 1M oxalic acid acetone solution
  9. filtrationfiltered
  10. customdried

출처 및 근거

ORD 기록
ord-d5f2435e215e49678958ca4a887b2658
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262427

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