Sodium borohydride → Tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate
Reaktionsgleichung
[C:1]([C:3]1[C:4]([CH3:29])=[C:5]([C:10](=[O:28])[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:13]2[CH2:25][CH2:26][OH:27])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[BH4-].[Na+]>CCO>[C:1]([C:3]1[C:4]([CH3:29])=[C:5]([CH:10]([OH:28])[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:14][CH:13]2[CH2:25][CH2:26][OH:27])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
tert-Butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-oxoethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate (3.81 g, 9.40 mmol) and dissolved in EtOH (60 mL) then NaBH4 (1.42 g, 37.6 mmol) was added and the mixture was stirred for 3 h. The ethanol was evaporated and brine was added then extracted with ethyl acetate twice. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by MPLC chromatography using a 330 g ISCO Redi-sep column with 5% MeOH/DCM solvent system to yield tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate: LC-MS (IE, m/z): 408 [M+1]+;