Borane → HCID 57655963, Verbindung
Reaktionsgleichung
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28](O)=[O:29])=[CH:24][CH:23]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([CH2:28][OH:29])=[CH:26][CH:27]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 3-tert-butoxycarbonyl-6-(4-carboxybenzylthio)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.85 g, 50% purity, 2.06 mmol) in anhydrous THF (40 mL) under nitrogen, add with stirring 1M borane in THF (4.2 mL) at 0° C. Warm to ambient temperature and stir 2-3 h. Quench by the careful addition of water (3 mL), dilute with saturated aqueous NaHCO3, extract three times with ethyl ether, dry over anhydrous MgSO4, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (5:1) to provide the title compound as a white solid (485 mg, 54%).