Reaktionsgleichung
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:9]([NH2:11])=[O:10])[CH2:2]2.C1(=O)O[CH:15]=[CH:14]O1>>[O:10]1[CH:15]=[CH:14][N:11]=[C:9]1[CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1Komponenten
Versuchsvorschrift
A stirred mixture of (±) 1-azabicyclo[2.2.2]octane-3-carboxamide (D2) (2.3 g; 0.015 moles) and vinylene carbonate (1.33 g; 0.016 moles) in polyphosphoric acid was placed in an oil bath at 120° and the temperature was raised to 180° over a period of 45 min. After cooling the reaction was treated with ice and washed with ether (100 ml). The pH of the aqueous solution was adjusted to 9 with 40% sodium hydroxide and potassium carbonate was then added until saturation point. Extraction with ether (4×100 ml) followed by drying (Na2SO4) and concentration in vacuo afforded a crude oil (1.45 g). Purification on neutral alumina (Brockmann grade 1) using a graded eluant of 2%-6% methanol in ethyl acetate produced the title compound as a pale yellow oil (0.74 g; 28%) which was converted into the oxalate salt, m.p. 98°-101° C. (acetone-methanol).
Aufarbeitung
- customwas placed in an oil bath at 120°
- temperaturethe temperature was raised to 180° over a period of 45 min
- temperatureAfter cooling the reaction
- additionwas treated with ice
- washwashed with ether (100 ml)
- additionwas then added until saturation point
- extractionExtraction with ether (4×100 ml)
- customby drying
- concentration(Na2SO4) and concentration in vacuo
- customafforded a crude oil (1.45 g)
- customPurification on neutral alumina (Brockmann grade 1)
Quellen und Nachweise
- ORD-Eintrag
- ord-5cdaf1c614934df68ec44f7fee454376
- Quelldatensatz
- uspto-grants-1990_11
- Patentnummer
- US04968691
Verknüpfte Notizen
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