Imidazole → 2-(5-triisopropylsilanyloxy-1H-indol-3-yl)-ethylamine

HRID 6746

Reaktionsgleichung

Reaktionsgleichung von HRID 6746
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[NH:6][CH:5]=1.N1C=CN=C1.[CH:19]([Si:22](Cl)([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])([CH3:21])[CH3:20]>CN(C)C=O.C(OCC)(=O)C>[CH:19]([Si:22]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[O:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][CH:5]=[C:4]2[CH2:3][CH2:2][NH2:1])([CH3:21])[CH3:20]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 5202SerotoninHCID 139400Triisopropylsilyl chloride

Produkt 1

HCID 220185062-(5-triisopropylsilanyloxy-1H-indol-3-yl)-ethylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-(2-amino-ethyl)-1H-indol-5-ol (3.0 g), imidazole (9.6 g), and triisopropylsilyl chloride (4.5 mL) was stirred in 20 mL N,N-dimethylformamide for 6 h. The solution was diluted with 100 mL of ethyl acetate and washed with 100 mL of sodium carbonate and 100 mL of saturated sodium chloride (3 times). The organic phase was dried over sodium sulfate and the solvent was evaporated. Silica gel chromatography (2% methyl alcohol in dichloromethane) gave 2-(5-triisopropylsilanyloxy-1H-indol-3-yl)-ethylamine (2.6 g). This compound was cyclized with formaldehyde by Procedure OO to afford 6-triisopropylsilanyloxy-2,3,4,9-tetrahydro-1H-β-carboline, which was protected with tert-butoxycarbonyl group by Procedure CC to give 6-triisopropylsilanyloxy-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester.

Aufarbeitung

  1. washwashed with 100 mL of sodium carbonate and 100 mL of saturated sodium chloride (3 times)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-5a7e3236c03546a79481668dbf1dafbb
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084154B2

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