Sodium borohydride → 1-(4-(6,7-Dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-4-(hydroxy(phenyl)methyl)pyrrolidin-2-one
Reaktionsgleichung
[C:1]([CH:9]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[C:30]4[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=4)[N:24]=[CH:23][CH:22]=3)=[C:16]([F:35])[CH:15]=2)[C:11](=[O:36])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH3:32][O:31][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][C:27]=1[O:33][CH3:34])[N:24]=[CH:23][CH:22]=[C:21]2[O:20][C:17]1[CH:18]=[CH:19][C:14]([N:12]2[CH2:13][CH:9]([CH:1]([OH:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:10][C:11]2=[O:36])=[CH:15][C:16]=1[F:35]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 4-benzoyl-1-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenyl)pyrrolidin-2-one (Example 47, 0.2 g, 0.41 mmol) in 15 mL of MeOH was slowly added solid NaBH4 (50 mg, 1.32 mmol). The reaction was stirred at RT for 1 h. The reaction was quenched with 10 mL of satd. NH4Cl solution. The solution was diluted with 100 mL of EtOAc and was washed with 30 mL of satd. NH4Cl followed by 30 mL of brine, dried over Na2SO4 and concentrated in vacuo. The crude solid was purified by chromatography (EtOAc to 5% MeOH/EtOAc) to give a colorless film. MS (ESI pos. ion) m/z: 489.3 (M+H). Calc'd Exact Mass for C28H25FN2O5: 488.51.