Reaktionsgleichung
[CH3:1][O:2][C:3]1([C:16](=[O:24])[C:17](=[N+]=[N-])[C:18](=[O:21])[CH2:19][CH3:20])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1>ClCCl.Cl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[O:24]=[C:16]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)[O:2][CH2:1][CH:17]1[C:18](=[O:21])[CH2:19][CH3:20]Komponenten
5
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
A solution of rhodium acetate dimer (0.002 g, 0.005 mmol) in dichloromethane (27 mL) was heated to 81° C. A solution of tert-butyl 4-methoxy-4-(2-diazo-1,3-dioxopent-1-yl)piperidine-1-carboxylate (0.092 g, 0.270 mmol) from Step D in dichloromethane (7 mL) was added slowly dropwise over 12 min. The reaction mixture was refluxed for 45 min then poured into IN hydrochloric acid, and extracted three times with dichloromethane. The organic layers were combined, washed with saturated sodium chloride solution, dried over sodium sulfite, filtered, and concentrated. The residue was purified by flash chromatography eluting with 10% ethyl acetate/dichloromethane to afford the title compound (0.034 g).
Aufarbeitung
- temperatureThe reaction mixture was refluxed for 45 min
- extractionextracted three times with dichloromethane
- washwashed with saturated sodium chloride solution
- dry with materialdried over sodium sulfite
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography
- washeluting with 10% ethyl acetate/dichloromethane
Quellen und Nachweise
- ORD-Eintrag
- ord-877888e2a7554dd4b0bc69673d1bcb3a
- Quelldatensatz
- uspto-grants-2006_08
- Patentnummer
- US07091211B2
Verknüpfte Notizen
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