Reaktionsgleichung
[N+](=[C:3]([C:7]([CH3:9])=[CH2:8])[C:4](=[O:6])[CH3:5])=[N-].[C:10]([O:14][C:15]([N:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>CCCCCC.C([O-])(=O)CCCCCCC.[Rh+2].C([O-])(=O)CCCCCCC>[C:4]([C:3]1[CH:21]2[N:17]([C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])[CH:18]([CH2:8][C:7]=1[CH3:9])[CH:19]=[CH:20]2)(=[O:6])[CH3:5]Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A solution of 3-diazo-4-methylpent-4-ene-2-one (2.30 g, 18.5 mmol) in hexane (25 ml) was added over 3 hours by means of a syringe pump to a stirred solution of N-tert-butoxycarbonyl pyrrole (9.18 g, 55 mmol) and rhodium(II) octanoate (0.07 g, 0.09 mmol) in refluxing hexane (10 ml) under an argon atmosphere. The mixture was refluxed for a further 1 hour period, and solvent was then removed using a rotary evaporator under reduced pressure. Purification of the product by silica gel column chromatography (using 2 parts diethyl ether and 8 parts petroleum ether, and 4 parts diethyl ether and 6 parts petroleum ether) yielded 2-acetyl-3-methyl-8-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]octa-2,6-diene, which is an orange liquid.
Aufarbeitung
- temperatureThe mixture was refluxed for a further 1 hour period
- customsolvent was then removed
- customa rotary evaporator under reduced pressure
- customPurification of the product by silica gel column chromatography (using 2 parts diethyl ether and 8 parts petroleum ether, and 4 parts diethyl ether and 6 parts petroleum ether)
Quellen und Nachweise
- ORD-Eintrag
- ord-4bdbba8cc48e4dc9afcc3959ff022dec
- Quelldatensatz
- uspto-grants-1993_07
- Patentnummer
- US05227385
Verknüpfte Notizen
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