Reacción #1622068

Ecuación de reacción

potassium carbonate

4(Aminocarbonylmethyl)-1-azabicyclo[2.2.1]heptane

vinylene carbonate

→

title compound

Rendimiento 7.0%

4-[(1,3-Oxazol-2-yl)methyl]-1-azabicyclo[2.2.1]heptane oxalate salt

Rendimiento 7.0%

Disolventes

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool
2. 2
   OtroThe product was recovered by extraction into chloroform
3. 3
   OtroThe organic phase was separated
4. 4
   Secadodried over sodium sulphate
5. 5
   Concentraciónconcentrated in vacuo to a gum (48mg)
6. 6
   workup.DISSOLUTIONThe gum was dissolved in ether
7. 7
   Filtraciónfiltered through a short column of decolourising charcoal
8. 8
   workup.ADDITIONtreated with oxalic acid (25mg) in methanol
9. 9
   Otroto crystallise

Procedimiento

4(Aminocarbonylmethyl)-1-azabicyclo[2.2.1]heptane (D27) (350mg, 0.00227 mole) in polyphosphoric acid (15g) was treated with vinylene carbonate (292mg, 0.0034 mole) with continuous stirring and the solution heated on an oil bath at 120° C. for 1.5h. The reaction was then allowed to cool and poured into aqueous saturated potassium carbonate solution. The product was recovered by extraction into chloroform. The organic phase was separated, dried over sodium sulphate and concentrated in vacuo to a gum (48mg). The gum was dissolved in ether, filtered through a short column of decolourising charcoal and treated with oxalic acid (25mg) in methanol. The solution was allowed to crystallise to afford the title compound (E14) (45mg, 0.00017 moles, 7%) as needles. M.pt. 140-143° C.

Fuente