Cyclohexene → tert-butyl N-[2-(pyridin-2-ylamino)ethyl]carbamate
Reaktionsgleichung
[C:1]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N+:13]=1[O-])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1CCCCC=1>CCO.[Pd]>[C:1]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
10% Pd/C (106.4 mg, 0.10 mmole) was added to a solution of 2-[[2-(Boc-amino)ethyl]amino]pyridine-N-oxide (126.7 mg, 0.5 mmole) and cyclohexene (0.25 mL, 0.25 mmole) in absolute EtOH (5 mL), and the mixture was heated to reflux. After 16 hr, the reaction was filtered through celite® and the filtrate was concentrated. The residue was combined with the residue obtained from a separate preparation (0.5 mmole scale), and the combined materials were purified by silica gel chromatography (5% MeOH/CHCl3). The title compound (148.4 mg, 63% based on 1 mmole of 2-[[2-(Boc-amino)ethyl]amino]pyridine-N-oxide) was obtained as a yellow oil: TLC (5% MeOH/CHCl3) Rf 0.43; 1H NMR (400, CDCl3) δ 8.05-8.12 (m, 1H), 7.37-7.46 (m, 1H), 6.53-6.61 (m, 1H), 6.41 (d, J=8.3 Hz, 1H), 5.12 (br s, 1H), 4.86 (br s, 1H), 3.26-3.51 (m, 4H), 1.44 (s, 9H); MS (ES) m/e 238 (M+H)+.
Aufarbeitung
- temperaturethe mixture was heated to reflux
- filtrationthe reaction was filtered through celite®
- concentrationthe filtrate was concentrated
- customobtained from a separate preparation (0.5 mmole scale)
- customthe combined materials were purified by silica gel chromatography (5% MeOH/CHCl3)
Quellen und Nachweise
- ORD-Eintrag
- ord-1bd10614f7804b869622645fd2730c2f
- Quelldatensatz
- uspto-grants-2001_02
- Patentnummer
- US06191304B1
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