Reacción #1160298

Ecuación de reacción

(±) 1-azabicyclo[2.2.2]octane-3-carboxamide

(±) 1-Azabicyclo[2.2.2]octane-3-carboxamide

vinylene carbonate

→

title compound

Rendimiento 28.0%

(±) 3-(1,3-Oxazol-2-yl)-1-azabicyclo[2.2.2]octane

Rendimiento 28.0%

Disolventes

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas placed in an oil bath at 120°
2. 2
   Temperaturathe temperature was raised to 180° over a period of 45 min
3. 3
   TemperaturaAfter cooling the reaction
4. 4
   workup.ADDITIONwas treated with ice
5. 5
   Lavadowashed with ether (100 ml)
6. 6
   workup.ADDITIONwas then added until saturation point
7. 7
   ExtracciónExtraction with ether (4×100 ml)
8. 8
   Otroby drying
9. 9
   Concentración(Na2SO4) and concentration in vacuo
10. 10
    Otroafforded a crude oil (1.45 g)
11. 11
    OtroPurification on neutral alumina (Brockmann grade 1)

Procedimiento

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).

Fuente