Sodium hydride → 5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridine-3-carbaldehyde
Reaktionsgleichung
[H-].[Na+].[F:3][C:4]1[CH:22]=[CH:21][C:7]([CH2:8][N:9]2[C@@H:14]([CH3:15])[CH2:13][N:12]([C:16](=[O:19])[CH2:17][OH:18])[C@H:11]([CH3:20])[CH2:10]2)=[CH:6][CH:5]=1.Cl[C:24]1[C:29]([CH:30]=[O:31])=[CH:28][C:27]([Cl:32])=[CH:26][N:25]=1>C1(C)C=CC=CC=1>[Cl:32][C:27]1[CH:28]=[C:29]([CH:30]=[O:31])[C:24]([O:18][CH2:17][C:16]([N:12]2[CH2:13][C@H:14]([CH3:15])[N:9]([CH2:8][C:7]3[CH:6]=[CH:5][C:4]([F:3])=[CH:22][CH:21]=3)[CH2:10][C@H:11]2[CH3:20])=[O:19])=[N:25][CH:26]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a 0° C. suspension of sodium hydride (60% dispersion in mineral oil, 0.031 g, 0.78 mmol) in toluene (3 mL) was added 1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-hydroxy-ethanone (0.20 g, 0.71 mmol) in toluene (2 mL). The reaction mixture was stirred at 0° C. for 30 minutes, and then treated with 2,5-dichloro-pyridine-3-carbaldehyde (0.14 g, 0.78 mmol). The resulting mixture was refluxed for 4 hours, cooled to ambient temperature and washed with saturated aqueous sodium hydrogen carbonate and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography provided the title compound (0.20 g).
Aufarbeitung
- temperatureThe resulting mixture was refluxed for 4 hours
- temperaturecooled to ambient temperature
- washwashed with saturated aqueous sodium hydrogen carbonate and brine
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-8d2580975c9440d99c5df9cc611230c9
- Quelldatensatz
- uspto-grants-2006_08
- Patentnummer
- US07098212B2
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