Tert-butyl 4-(2-ethoxy-2-oxoethyl)-4-(nitromethyl)piperidine-1-carboxylate → Tert-butyl 3-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate
Reaktionsgleichung
C([O:3][C:4](=O)[CH2:5][C:6]1([CH2:19][N+:20]([O-])=O)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)C>C(O)C.[Ni]>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][C:6]2([CH2:19][NH:20][C:4](=[O:3])[CH2:5]2)[CH2:7][CH2:8]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of tert-butyl 4-(2-ethoxy-2-oxoethyl)-4-(nitromethyl)piperidine-1-carboxylate (330 g, 990 mmol, 1.00 equiv, 99%) and Ni (40 g, 0.15 equiv) in ethanol (1200 mL) was stirred for 24 h under a hydrogen atmosphere at room temperature. The solid was filtered out. The filtrate was concentrated under vacuum. The crude product was purified by re-crystallization from ether to afford the title compound. LC-MS (ES, m/z): 199 [M+H]+; H-NMR (400 MHz, CDCl3, ppm): 1.447-1.476 (9H, s), 1.597-1.673 (4H, m, J=30.4 Hz), 2.235 (2H, s), 3.226 (2H, s), 3.284-3.348 (2H, m, J=25.6 Hz), 3.507-3.567 (2H, m, J=24 Hz), 6.048 (1H, s).