Aluminium lithium hydride → 5-methyl-3-(pyrrolidin-3-yl)-1H-indole

HRID 1526161

반응식

HRID 1526161 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH:17]1[CH2:21][C:20](=O)[NH:19][C:18]1=O>C1COCC1>[CH3:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH:17]1[CH2:21][CH2:20][NH:19][CH2:18]1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 670364713-(5-methyl-1H-indol-3-yl)pyrrolidine-2,5-dione

생성물 1

HCID 548571365-methyl-3-(pyrrolidin-3-yl)-1H-indole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Lithium aluminum hydride (7.9 g, 200 mmol) in dry THF (380 mL) was stirred for 20 min. at RT under nitrogen atmosphere. 3-(5-Methyl-1H-indol-3-yl) pyrrolidine-2,5-dione (9.5 g, 41 mmol) was added portionwise and the reaction mixture was heated to reflux overnight. The reaction mixture was cooled to RT, quenched with aqueous sodium sulfate, and filtered. The solid was rinsed with THF and the THF layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography (25% MeOH/DCM/ammonia) to afford the title compound. Yield: 4.2 g, 49.2%.

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customquenched with aqueous sodium sulfate
  4. filtrationfiltered
  5. washThe solid was rinsed with THF
  6. dry with materialthe THF layer was dried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (25% MeOH/DCM/ammonia)

출처 및 근거

ORD 기록
ord-94cff7cb40044d7c9792b5114600280d
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085580B2

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