反应详情

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).

1. customwas placed in an oil bath at 120°
2. temperaturethe temperature was raised to 180° over a period of 45 min
3. temperatureAfter cooling the reaction
4. additionwas treated with ice
5. washwashed with ether (100 ml)
6. additionwas then added until saturation point
7. extractionExtraction with ether (4×100 ml)
8. customby drying
9. concentration(Na2SO4) and concentration in vacuo
10. customafforded a crude oil (1.45 g)
11. customPurification on neutral alumina (Brockmann grade 1)