Reaktionsgleichung
[CH:1]1[C:12]2[CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=O)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]1[C:12]2[CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a suspension of 11,12-dihydro-5H-dibenzo[b,f]azocin-6-one (2.0 g, 8.96 mmol) in dry THF (20 ml) is added dropwise a solution of LiAlH4 (1.0 N in THF, 8.96 ml) over a period of 10 min. After ceasing of gas evolution, the reaction mixture is kept stirring at reflux overnight, then quenched by the addition of water (0.48 ml). The precipitate is filtered off and the filtrate is extracted twice with EtOAc. The combined organic layers are dried over Na2SO4, the solvent is evaporated and the residue recrystallized from boiling hexane to give off white crystals of the title compound (1.35 g) in 72% yield: tR (LC-2) 1.65 min; ESI-MS(+): m/z 210.70 [M+H]+ (calcd 209.29 for C15H15N).
Aufarbeitung
- temperatureat reflux overnight
- customquenched by the addition of water (0.48 ml)
- filtrationThe precipitate is filtered off
- extractionthe filtrate is extracted twice with EtOAc
- dry with materialThe combined organic layers are dried over Na2SO4
- customthe solvent is evaporated
- customthe residue recrystallized
Quellen und Nachweise
- ORD-Eintrag
- ord-ffb5ce934f784021b5353f7493e157f7
- Quelldatensatz
- uspto-grants-2011_03
- Patentnummer
- US07897788B2
Verknüpfte Notizen
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