Tryptophol → N-[1-(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)ethyl]acetamide

HRID 647587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 647587
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][OH:12])=[CH:2]1.[CH3:13][CH:14]([NH:18][C:19](=[O:21])[CH3:20])[C:15](=O)[CH3:16]>B(F)(F)F.CCOCC.C1C=CC=CC=1>[CH3:16][C:15]1([CH:14]([NH:18][C:19](=[O:21])[CH3:20])[CH3:13])[C:2]2[NH:1][C:9]3[C:4]([C:3]=2[CH2:10][CH2:11][O:12]1)=[CH:5][CH:6]=[CH:7][CH:8]=3

Komponenten

5

Edukt 2

HCID 10685TryptopholHCID 97923N-(1-methyl-2-oxopropyl)acetamide

Produkt 1

HCID 12708188N-[1-(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)ethyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8000Boron trifluoride etherateKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of indole-3-ethanol (16.1 g), benzene (1200 ml), N-(1-methyl-2-oxopropyl)-acetamide[12.7 g, described by A. Triebs and W. Sutter, Chem. Ber. 84, 96(1951)] and boron trifluoride-etherate (5 drops) is refluxed using a water separating condenser for 60 minutes. After cooling, the mixture is washed with concentrated sodium bicarbonate, dried over magnesium sulfate and evaporated. The residue is chromatographed on silica gel using chloroform. The eluates are evaporated to give a residue of the title compound as a 1:1 mixture of diastereoisomers:

Aufarbeitung

  1. customfor 60 minutes
  2. temperatureAfter cooling
  3. washthe mixture is washed with concentrated sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on silica gel
  7. customThe eluates are evaporated

Quellen und Nachweise

ORD-Eintrag
ord-95788004af7e4f22990074913ccd93f3
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04409224

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