Reacción #8674

Ecuación de reacción

10-oxa-4-azatricyclo[5.2.1.02,6]decane-3,5-dione

10-Oxa-4-azatricyclo[5.2.1.02,6] decane-3,5-dione

lithium aluminum hydride

sodium chloride

→

10-Oxa-4-azatricyclo[5.2.1.02,6]decane

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled in an ice bath
2. 2
   workup.DISTILLATIONdistilled water
3. 3
   Filtraciónthe resulting suspension is filtered
4. 4
   Lavadothe solid is washed with ethyl acetate
5. 5
   OtroThe organic phase of the filtrate is separated off
6. 6
   Extracciónthe aqueous phase is extracted once more with ethyl acetate
7. 7
   OtroThe combined organic phases are dried
8. 8
   Filtraciónfiltered
9. 9
   Otrothe solvent is removed in vacuo
10. 10
    Filtraciónfiltered
11. 11
    Lavadowashed with diethyl ether
12. 12
    Otrodried
13. 13
    Otro730 mg (13% of theory) of the product are obtained

Procedimiento

5.00 g (29.91 mmol) of 10-oxa-4-azatricyclo[5.2.1.02,6]decane-3,5-dione (example IV, step 1) were suspended in 150 ml of absolute THF under argon and cooled in an ice bath. 2.27 g (59.82 mmol) of lithium aluminum hydride are added in portions, and the mixture is stirred at 0° C. overnight. The reaction solution is hydrolyzed with saturated sodium chloride solution and distilled water, the resulting suspension is filtered, and the solid is washed with ethyl acetate. The organic phase of the filtrate is separated off, and the aqueous phase is extracted once more with ethyl acetate. The combined organic phases are dried and filtered, and the solvent is removed in vacuo. The residue is suspended in diethyl ether, filtered, washed with diethyl ether and dried. 730 mg (13% of theory) of the product are obtained.

Fuente