反应详情

A stirred mixture of 1-azabicyclo[3.2.1]oct-5-ylcarboxamide (D20, 1.50 g, 0.0097 mole) and vinylene carbonate (1.2 g, 0.014 mole) in polyphosphoric acid (35 g) was heated at 120°-130° C. for 2h. The reaction mixture was allowed to cool, then treated with ice, before basifying with potassium carbonate solution. The aqueous was shaken well with ether, then the mixture filtered and the organic layer separated. The aqueous was again extracted with ether (2×80 ml) and all the ether extracts combined, dried (Na2SO4) and concentrated in vacuo to leave a yellow oil. This was chromatographed on a basic alumina column eluting with ethyl acetate and the material obtained converted to its oxalate salt and recrystallised from methanol/ether to give the title compound (E12) as a white solid (410 mg, 16%) m.p. 143°-145° C.

1. temperaturewas heated at 120°-130° C. for 2h
2. temperatureto cool
3. additiontreated with ice
4. filtrationthe mixture filtered
5. customthe organic layer separated
6. extractionThe aqueous was again extracted with ether (2×80 ml) and all the ether
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated in vacuo
9. customto leave a yellow oil
10. customThis was chromatographed on a basic alumina column
11. washeluting with ethyl acetate
12. customthe material obtained
13. customrecrystallised from methanol/ether