Borane,N-dimethylmethanamine (1:1) → 4-tert-Butyl-2-(1-Boc-piperidin-4-yloxy)benzyl Alcohol
Reaktionsgleichung
[B-][N+](C)(C)C.[C:6]([C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[C:12]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)[CH:11]=1)([CH3:9])([CH3:8])[CH3:7]>O1CCCC1>[C:6]([C:10]1[CH:18]=[CH:17][C:13]([CH2:14][OH:15])=[C:12]([O:19][CH:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]2)[CH:11]=1)([CH3:9])([CH3:7])[CH3:8]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of borane-trimethylamine complex (1.35 mL of a 1 M solution in tetrahydrofuran) in tetrahydrofuran (3 mL) stirring at 0° C., a solution of 4-(tert-butyl)-2-(1-Boc-piperidine-4-yloxy)benzoic acid (0.51 g, 1.35 mmol) in tetrahydrofuran (7 mL) was added slowly via cannula. After the addition was complete the reaction mixture was stirred at room temperature for 4 h, then an additional amount of borane-trimethylamine complex was added (1.35 mL of a 1 M solution in tetrahydrofuran). The reaction mixture was stirred at room temperature for another 2 h. After quenching with ice, the mixture was partitioned between brine and dichloromethane. The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated in vacuo to a residue (0.42 g, 86%) which was identified as the title compound and used directly in the next step without further purification.