Sodium borohydride → N-(4-fluoro-3-trifluoromethyl-benzyl)-N-[3-(1-hydroxy-ethyl)-benzo[b]thiophen-2-yl]-ethanesulfonamide
Reaktionsgleichung
[BH4-].[Na+].[C:3]([C:6]1[C:7]2[CH:32]=[CH:31][CH:30]=[CH:29][C:8]=2[S:9][C:10]=1[N:11]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=1)[S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])(=[O:5])[CH3:4]>C(O)C>[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:11]([C:10]2[S:9][C:8]3[CH:29]=[CH:30][CH:31]=[CH:32][C:7]=3[C:6]=2[CH:3]([OH:5])[CH3:4])[S:12]([CH2:15][CH3:16])(=[O:13])=[O:14])=[CH:19][C:20]=1[C:25]([F:28])([F:26])[F:27]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Sodium borohydride (0.14 g, 3.7 mmol) was added to a solution of N-(3-acetyl-benzo[b]thiophen-2-yl)-N-(4-fluoro-3-trifluoromethyl-benzyl)-ethanesulfonamide (0.268 g, 0.582 mmol) in ethanol (10 mL), and the resulting mixture was stirred at room temperature for 3 h. The solvent was evaporated, the residue partitioned between dichloromethane and water, the organic layer separated, dried over sodium sulfate, filtered, and the solvent evaporated in vacuo to yield a residue. The residue was purified by flash column chromatography (SiO2), eluting with an ethyl acetate-heptane (10-40%) gradient to yield N-(4-fluoro-3-trifluoromethyl-benzyl)-N-[3-(1-hydroxy-ethyl)-benzo[b]thiophen-2-yl]-ethanesulfonamide as a colorless solid.