Potassium Carbonate → Tert-butyl 3-(4-bromo-2,5-difluorophenoxy)-2-oxo-1,4'-bipiperidine-1'-carboxylate
Reaktionsgleichung
Br[CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[C:3]1=[O:21].C([O-])([O-])=O.[K+].[K+].[Br:28][C:29]1[C:34]([F:35])=[CH:33][C:32]([OH:36])=[C:31]([F:37])[CH:30]=1>CN(C=O)C.O.CCOC(C)=O>[Br:28][C:29]1[C:34]([F:35])=[CH:33][C:32]([O:36][CH:2]2[CH2:7][CH2:6][CH2:5][N:4]([CH:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)[C:3]2=[O:21])=[C:31]([F:37])[CH:30]=1Komponenten
7
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
To a solution of tert-butyl 3-bromo-2-oxo-1,4′-bipiperidine-1′carboxylate (723 mg, 2.00 mmol) in DMF (5 mL) was added K2CO3 (553 mg, 4.00 mmol) and 4-bromo-2,5-difluorophenol (460 mg, 2.20 mmol). The reaction was heated at 60° C. overnight. The reaction was cooled and diluted with water and EtOAc. The organic layer was separated and the aqueous washed with EtOAc. The combined organic layers were dried with MgSO4 and concentrated. The crude residue was purified over silica gel (2:1 hexanes/EtOAc) to give tert-butyl 3-(4-bromo-2,5-difluorophenoxy)-2-oxo-1,4′-bipiperidine-1′-carboxylate (710 mg, 73%) as a white solid.
Aufarbeitung
- temperatureThe reaction was cooled
- customThe organic layer was separated
- washthe aqueous washed with EtOAc
- dry with materialThe combined organic layers were dried with MgSO4
- concentrationconcentrated
- customThe crude residue was purified over silica gel (2:1 hexanes/EtOAc)
Quellen und Nachweise
- ORD-Eintrag
- ord-200bb0d81cbf451086bc699006b70819
- Quelldatensatz
- uspto-grants-2014_06
- Patentnummer
- US08754226B2
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