Sodium Hydroxide → 5,5-dimethyl-2,3,4,5-tetrahydro-1H-1-benzazepine
Reaktionsgleichung
[CH3:1][C:2]1([CH3:14])[CH2:8][CH2:7][C:6](=O)[NH:5][C:4]2[CH:10]=[CH:11][CH:12]=[CH:13][C:3]1=2.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>O.C1COCC1>[CH3:1][C:2]1([CH3:14])[CH2:8][CH2:7][CH2:6][NH:5][C:4]2[CH:10]=[CH:11][CH:12]=[CH:13][C:3]1=2Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
5,5-Dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (1.5 g, 8.0 mmol) was dissolved into THF (20 ml) and cooled down to 0° C. LAH (0.5 g 60% in oil, 13 mmol) was added in portions. The reaction was heated to reflux for 2 h. TLC showed a new spot alongside staring lactam. Another 360 mg of LAH was added and the mixture was heated for 2 h. H2O was added until sizzling stopped followed by 2N NaOH. Stirred for 15 min at RT. Na2SO4 (3.8 g) was added and the mixture was stirred for 15 min followed by filtration over Celite®. Diluted with EtOAc and washed with H2O, dried (MgSO4), filtered and concentrated to give 5,5-Dimethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine.
Aufarbeitung
- temperatureThe reaction was heated
- temperatureto reflux for 2 h
- temperaturethe mixture was heated for 2 h
- stirringthe mixture was stirred for 15 min
- filtrationfollowed by filtration over Celite®
- additionDiluted with EtOAc
- washwashed with H2O
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-9d0d82ddc0e04ca0a25d7e7b44c8bde8
- Quelldatensatz
- uspto-grants-2012_08
- Patentnummer
- US08247556B2
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