Sodium Hydroxide → (1S,6S)-1-Amino-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-ene
Reaktionsgleichung
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[NH2:15][C@:16]12[CH2:24][N:23]([C@@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[C:22](=O)[C@@H:21]1[CH2:20][CH:19]=[CH:18][CH2:17]2.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH2:15][C@:16]12[CH2:24][N:23]([C@@H:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH3:26])[CH2:22][C@@H:21]1[CH2:20][CH:19]=[CH:18][CH2:17]2Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
A 65% solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene (2.87 mL, 9.56 mmol) was added to a solution of (1S,6R)-1-amino-7-oxo-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-ene (612 mg, 2.39 mmol) in toluene (11.9 mL), and the mixture was stirred at 80° C. for one hour. A 5 mol/L sodium hydroxide solution (15.0 mL) was added to the reaction solution with stirring under ice-cooling, followed by extraction with toluene (30 mL×2). The organic layer was washed with brine (90 ml) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give 450 mg of the title compound.
Aufarbeitung
- stirringwith stirring under ice-
- temperaturecooling
- extractionfollowed by extraction with toluene (30 mL×2)
- washThe organic layer was washed with brine (90 ml)
- dry with materialdried over anhydrous sodium sulfate
- filtrationAfter filtration
- concentrationthe filtrate was concentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-63c09dcb08bb42f49e95d7b1253e081d
- Quelldatensatz
- uspto-grants-2013_12
- Patentnummer
- US08618094B2
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