تفاعل #741709

معادلة التفاعل

1-azabicyclo[3.2.1]oct-5-ylcarboxamide

vinylene carbonate

potassium carbonate

→

title compound

المردود 16.0%

5-(1,3-Oxazol-2-yl)-1-azabicyclo[3.2.1]octane oxalate salt

المردود 16.0%

المذيبات

—

polyphosphoric acid

ether

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated at 120°-130° C. for 2h
2. 2
   درجة الحرارةto cool
3. 3
   workup.ADDITIONtreated with ice
4. 4
   ترشيحthe mixture filtered
5. 5
   أخرىthe organic layer separated
6. 6
   استخلاصThe aqueous was again extracted with ether (2×80 ml) and all the ether
7. 7
   تجفيفdried (Na2SO4)
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىto leave a yellow oil
10. 10
    أخرىThis was chromatographed on a basic alumina column
11. 11
    غسيلeluting with ethyl acetate
12. 12
    أخرىthe material obtained
13. 13
    أخرىrecrystallised from methanol/ether

الإجراء التجريبي

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.

المصدر