Sodium cyanoborohydride → 1H-Indole, 4-(difluoromethoxy)-2,3-dihydro-
Reaktionsgleichung
C([BH3-])#N.[Na+].[F:5][CH:6]([F:17])[O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][NH:12]2>FC(F)(F)C(O)=O>[F:17][CH:6]([F:5])[O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH2:10][CH2:11][NH:12]2Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
0.722 mg of sodium cyanoborohydride is added to a solution of 1 g of 4-difluoromethoxy-1H-indole in 15 ml of trifluoroacetic acid, cooled to 0° C., and the stirring is continued for 3 hours. The reaction mixture is then concentrated under reduced pressure, treated with a concentrated sodium hydroxide solution, extracted with dichloromethane, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica column chromatography, elution being carried out with a mixture of heptane and ethyl acetate (20/80: v/v), so as to give 300 mg of 4-difluoromethoxy-2,3-dihydro-1H-indole in the form of a yellow oil, the characteristics of which are the following:
Aufarbeitung
- concentrationThe reaction mixture is then concentrated under reduced pressure
- additiontreated with a concentrated sodium hydroxide solution
- extractionextracted with dichloromethane
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue is purified by silica column chromatography, elution
- additionbeing carried out with a mixture of heptane and ethyl acetate (20/80: v/v)
Quellen und Nachweise
- ORD-Eintrag
- ord-4bb71e9b6e0d4e118bd5b6c79c75b6f8
- Quelldatensatz
- uspto-grants-2015_09
- Patentnummer
- US09133168B2
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