Reaktionsgleichung
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=[O:19])[CH:8]=1.[N+:20]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])(C(OC(C)(C)C)=O)=[N-:21].[Cl-].[NH4+].CN(C)[CH:40]=[O:41]>>[C:2]([O:4][C:40]([N:21]([C:13]1([C:9]2[CH:8]=[N:7][CH:12]=[CH:11][CH:10]=2)[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[O:19])[NH:20][C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])=[O:41])([CH3:5])([CH3:3])[CH3:1]Komponenten
Reaktionsbedingungen
- Temperatur
- 20 °C
Versuchsvorschrift
Potassium t-butoxide (3.7 g, 33 mmol) was added, in one portion, to a stirred solution of 2-(pyrid-3-yl)cyclohexanone (5.3 g, 30 mmol) in dimethylformamide (60 ml) at 0° C. After 60 minutes the dark red solution was treated with di-t-butyl diazodicarboxylate (7.6 g, 33 mmol) over 5 minutes. The mixture was then allowed to warm to 20° C. over 1 hour, poured into saturated ammonium chloride solution (50 ml) and extracted with ethyl acetate (2×25 ml). The combined organic extracts were successively washed with water (20 ml) and saturated brine (20 ml) and dried over sodium sulphate. Concentration in vacuo gave the crude product which was recrystallised from petroleum ether (60°-80° C.; 150 ml) to give 2-(N,N'-di-t-butoxycarbonylhydrazino)-2-(pyrid-3-yl)cyclohexanone (7.1 g, 17.5 mmol), m.p. 123°-125° C.;
Aufarbeitung
- extractionextracted with ethyl acetate (2×25 ml)
- washThe combined organic extracts were successively washed with water (20 ml) and saturated brine (20 ml)
- dry with materialdried over sodium sulphate
- concentrationConcentration in vacuo
- customgave the crude product which
- customwas recrystallised from petroleum ether (60°-80° C.; 150 ml)
Quellen und Nachweise
- ORD-Eintrag
- ord-78a762870ee1455c8af616941c81c009
- Quelldatensatz
- uspto-grants-1994_01
- Patentnummer
- US05276046
Verknüpfte Notizen
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