Methanol → 3-cyclohexyl-1H-indole-6-carboxylic Acid

HRID 747933Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747933
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.CO>C1COCC1>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 111840773-(Cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acid

Produkt 1

HCID 112419893-cyclohexyl-1H-indole-6-carboxylic AcidAusbeute 79,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-Cyclohexenyl-1H-indole-6-carboxylic acid (38 g) was added to a Parr bottle, followed by methanol (100 mL) and THF (100 mL). The bottle was flushed with argon and 10% palladium on carbon (1.2 g) was added. The flask was then evacuated and subsequently refilled with H2 to a pressure of 55 psi, and the resultant mixture was shaken for 18 hours at RT. The catalyst was then removed by filtration through celite. Concentration of the filtrate provided the desired product as a pale purple solid (30.6 g, 79%). ESI-MS m/z 244 (MH+).

Aufarbeitung

  1. customThe bottle was flushed with argon and 10% palladium on carbon (1.2 g)
  2. additionwas added
  3. customThe flask was then evacuated
  4. additionsubsequently refilled with H2 to a pressure of 55 psi
  5. customThe catalyst was then removed by filtration through celite

Quellen und Nachweise

ORD-Eintrag
ord-fde7538390954263887bc0b131aacdbb
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399758B2

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