Acetic Anhydride → 1-(2,3-Dihydro-6-methoxy-1H-indol-1-yl)ethanone

HRID 1014337노트

반응식

HRID 1014337 반응식
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[BH3-]C#N.[Na+].[C:16](OC(=O)C)(=[O:18])[CH3:17]>C(O)(=O)C>[C:16]([N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[CH2:7][CH2:8]1)(=[O:18])[CH3:17]

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 766596-Methoxy-1H-indoleHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 594419921-(2,3-Dihydro-6-methoxy-1H-indol-1-yl)ethanone

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

To a solution of 6-(methyloxy)-1H-indole (5.0 g, 34 mmols) in acetic acid (150 mL) was added NaBH3CN (5.12 g, 81.6 mmol) in several small portions. After stirring overnight at rt, the solvent was removed, the residue redissolved in ethyl acetate (300 mL), washed with saturated NaHCO3 (600 mL), filtered through a cotton plug and concentrated under reduced pressure to provide the crude indoline. ESIMS (M+H)+=150. The residue was then dissolved in glacial acetic acid (150 mL) and acetic anhydride (3.45 g, 33.86 mmol) was added. After stirring at rt for two hrs, the solvent was removed, residue resuspended in ethyl acetate (200 mL), washed with saturated NaHCO3 (600 mL). The aqueous layer was extracted with ethyl acetate (200 mL). The organic layers were combined, filtered through a cotton plug, and concentrated under reduced pressure to provide 1-acetyl-6-(methyloxy)-2,3-dihydro-1H-indole which was used without any further purification. ESIMS (M+H)+=192.

후처리

  1. customthe solvent was removed
  2. dissolutionthe residue redissolved in ethyl acetate (300 mL)
  3. washwashed with saturated NaHCO3 (600 mL)
  4. filtrationfiltered through a cotton plug
  5. concentrationconcentrated under reduced pressure
  6. customto provide the crude indoline
  7. stirringAfter stirring at rt for two hrs
  8. customthe solvent was removed
  9. washwashed with saturated NaHCO3 (600 mL)
  10. extractionThe aqueous layer was extracted with ethyl acetate (200 mL)
  11. filtrationfiltered through a cotton plug
  12. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e66e4b9032c84c608f10f09633cf04f7
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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