Phenethyl tosylate → 1-phenethyl-3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indole

HRID 1766239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766239
[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH:18]1[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1)(C(C)(C)C)(C)C.[H-].[K+].S(C1C=CC(C)=CC=1)(O[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=O)=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:31]([N:14]1[C:15]2[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=2)[C:12]([CH:18]2[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]2)=[CH:13]1)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Komponenten

6

Edukt 4

HCID 20522Phenethyl tosylateHCID 82127Potassium hydride2×HCID 2724141Tetrabutylammonium FluorideHCID 179801335-(t-Butyldimethylsilanyloxy)-3-(1-methylpiperidin-4-yl)-1H-indol

Produkt 1

HCID 179801211-phenethyl-3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indoleAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To solution of 5-(t-butyldimethylsilanyloxy)-3-(1-methylpiperidin-4-yl)-1H-indol (285 mg, 0.83 mmol) in tetrahydrofuran (20 mL) stirring at 0° C. was treated with potassium hydride (99 mg of a 35% dispersion in oil, 0.87 mmol). The light yellow solution was stirred for 20 minutes at 0° C. Phenethyl tosylate (2.29 g, 8.30 mmol) was added and stirred at 0° C. for 3 h, and at room temperature overnight. Addition 35% potassium hydride (94 mg, 0.83 mmol) was added and the reaction was stirred at room temperature overnight. The mixture was treated with tetrabutylammonium fluoride (830 μL of a 1M solution in tetrahydrofuran, 0.83 mmol) and was stirred overnight at room temperature, before concentrating in vacuo. Purification by silica gel chromatography 9:1 dichloromethane: methanol gave 175 mg (63%) of the title compound as orange foam: MS (APCI): m/e 335.2 (M+1).

Aufarbeitung

  1. stirringstirred at 0° C. for 3 h
  2. customat room temperature
  3. customovernight
  4. additionwas added
  5. stirringthe reaction was stirred at room temperature overnight
  6. stirringwas stirred overnight at room temperature
  7. concentrationbefore concentrating in vacuo
  8. customPurification by silica gel chromatography 9:1 dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-05ce864a61d645a2b912a3f02d27210e
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230011B2

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