Reaction #8674

Reaction equation

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

Solvents

THF

Conditions

Workup

1. 1
   Temperaturecooled in an ice bath
2. 2
   workup.DISTILLATIONdistilled water
3. 3
   Filtrationthe resulting suspension is filtered
4. 4
   Washthe solid is washed with ethyl acetate
5. 5
   OtherThe organic phase of the filtrate is separated off
6. 6
   Extractionthe aqueous phase is extracted once more with ethyl acetate
7. 7
   OtherThe combined organic phases are dried
8. 8
   Filtrationfiltered
9. 9
   Otherthe solvent is removed in vacuo
10. 10
    Filtrationfiltered
11. 11
    Washwashed with diethyl ether
12. 12
    Otherdried
13. 13
    Other730 mg (13% of theory) of the product are obtained

Procedure

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