1-(Tert-butoxycarbonyl)-4-(4-phenylbutylidene)piperidine → 1-(Tert-butoxycarbonyl)-4-(4-phenylbutyl)piperidine
Reaktionsgleichung
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of 1-(tert-butoxycarbonyl)-4-(4-phenylbutylidene)piperidine (216 mg, 0.69 mmol) in MeOH (10 mL) was added 20% Pd(OH)2/C (50 mg). The mixture was warmed to reflux under a H2 atmosphere for 6 h. After filtration and concentration, 1-(tert-butoxycarbonyl)-4-(4-phenylbutyl)piperidine was obtained (202 mg, 92%) as a pale yellow oil, which was used in the following step without purification. 1H NMR (CDCl3, 400 MHz) δ 7.27 (m, 2H), 7.19 (m, 3H), 4.07 (d, 2H, J=12.0 Hz), 2.63 (m, 4H), 1.57 (m, 3H), 1.46 (s, 9H), 1.34 (m, 3H), 1.24 (m, 3H), 1.06 (m, 2H).