Reaktion #8674

Reaktionsgleichung

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled in an ice bath
2. 2
   workup.DISTILLATIONdistilled water
3. 3
   Filtrationthe resulting suspension is filtered
4. 4
   Waschenthe solid is washed with ethyl acetate
5. 5
   SonstigeThe organic phase of the filtrate is separated off
6. 6
   Extraktionthe aqueous phase is extracted once more with ethyl acetate
7. 7
   SonstigeThe combined organic phases are dried
8. 8
   Filtrationfiltered
9. 9
   Sonstigethe solvent is removed in vacuo
10. 10
    Filtrationfiltered
11. 11
    Waschenwashed with diethyl ether
12. 12
    Sonstigedried
13. 13
    Sonstige730 mg (13% of theory) of the product are obtained

Vorschrift

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.

Quelle