Réaction #8674

Équation de réaction

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

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Températurecooled in an ice bath
2. 2
   workup.DISTILLATIONdistilled water
3. 3
   Filtrationthe resulting suspension is filtered
4. 4
   Lavagethe solid is washed with ethyl acetate
5. 5
   AutreThe organic phase of the filtrate is separated off
6. 6
   Extractionthe aqueous phase is extracted once more with ethyl acetate
7. 7
   AutreThe combined organic phases are dried
8. 8
   Filtrationfiltered
9. 9
   Autrethe solvent is removed in vacuo
10. 10
    Filtrationfiltered
11. 11
    Lavagewashed with diethyl ether
12. 12
    Autredried
13. 13
    Autre730 mg (13% of theory) of the product are obtained

Mode opératoire

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.

Source