Sodium cyanoborohydride → HCID 87604005, Verbindung
Reaktionsgleichung
C([BH3-])#N.[Na+].[C:5]([O:9][C:10]([N:12]1[CH:17]=[C:16]([C:18]2([CH2:29][C:30]3[CH:35]=[C:34]([Cl:36])[N:33]=[C:32]([Cl:37])[CH:31]=3)[C:26]3[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=3)[NH:20][C:19]2=[O:28])[CH2:15][CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>C(O)(=O)C>[C:5]([O:9][C:10]([N:12]1[CH:17]=[C:16]([C:18]2([CH2:29][C:30]3[CH:35]=[C:34]([Cl:36])[N:33]=[C:32]([Cl:37])[CH:31]=3)[C:26]3[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=3)[NH:20][C:19]2=[O:28])[CH:15]=[CH:14][CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
Sodium cyanoborohydride (0.37 g, 5.89 mmol) was added to a solution of rac-5-[6-chloro-3-(2,6-dichloro-pyridin-4-ylmethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.3 g, 0.589 mmol) (from Example 23 supra) in acetic acid (6 mL). The mixture was heated at 60° C. for 16 hours. After cooling, the solvent was evaporated in vacuo. To the residue was added saturated aqueous sodium bicarbonate solution, and extracted three times with ethyl acetate. The organic layers were separated, combined, dried over Na2SO4 and concentrated. The residue was purified by chromatography (ethyl acetate-dichloromethane, 1:9, V/V) to give rac-5-[6-chloro-3-(2,6-dichloro-pyridin-4-ylmethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-pyridine-1-carboxylic acid tert-butyl ester as a white solid. (Yield 0.2 g, 67%). Further purification by recrystallization from dichloromethane-hexanes gave the product as a white solid. (Yield 0.075 g).