반응 #8674

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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

용매

THF

반응 조건

후처리

1. 1
   온도cooled in an ice bath
2. 2
   workup.DISTILLATIONdistilled water
3. 3
   여과the resulting suspension is filtered
4. 4
   세척the solid is washed with ethyl acetate
5. 5
   기타The organic phase of the filtrate is separated off
6. 6
   추출the aqueous phase is extracted once more with ethyl acetate
7. 7
   기타The combined organic phases are dried
8. 8
   여과filtered
9. 9
   기타the solvent is removed in vacuo
10. 10
    여과filtered
11. 11
    세척washed with diethyl ether
12. 12
    기타dried
13. 13
    기타730 mg (13% of theory) of the product are obtained

실험 절차

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.

출처