Aluminium lithium hydride → [5-(2-dimethylamino-ethoxy)-1H-indol-2-yl]-methanol

HRID 1790894

Reaktionsgleichung

Reaktionsgleichung von HRID 1790894
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([O:21][CH2:22][C:23](=O)[N:24]([CH3:26])[CH3:25])=[CH:16][CH:15]=2)=O)C>O1CCCC1>[CH3:25][N:24]([CH3:26])[CH2:23][CH2:22][O:21][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH2:10][OH:9])=[CH:20]2

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 695870655-dimethylcarbamoylmethoxy-1H-indole-2-carboxylic acid ethyl ester

Produkt 1

HCID 22042139[5-(2-dimethylamino-ethoxy)-1H-indol-2-yl]-methanolAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium aluminum hydride (1.7 g, 45 mmol) was added to 5-dimethylcarbamoylmethoxy-1H-indole-2-carboxylic acid ethyl ester (1.4 g, 4.8 mmol) in tetrahydrofuran (80 mL). The mixture was stirred at room temperature for 4 hours and cooled to 0° C. It was then quenched with water (1.7 mL), 15% sodium hydroxide (1.7 mL) and water (1.7 mL). The precipitate was filtered off and the filtrate was concentrated to give 0.6 g (54%) of [5-(2-dimethylamino-ethoxy)-1H-indol-2-yl]-methanol.

Aufarbeitung

  1. temperaturecooled to 0° C
  2. customIt was then quenched with water (1.7 mL), 15% sodium hydroxide (1.7 mL) and water (1.7 mL)
  3. filtrationThe precipitate was filtered off
  4. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-b5c9fd879bc148bb9d2bae474ded4855
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071332B2

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