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

HRID 918897

Reaktionsgleichung

Reaktionsgleichung von HRID 918897
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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%.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-0a63783d039e4223ae006b1871f57cff
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09271971B2

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