반응 #64283

반응 방정식

HCl

2,8-dimethyl-1-oxa-8-azaspiro[4,5]-decan-3-one

sodium borohydride

→

ammonia

3-hydroxy-2,8-dimethyl-1-oxa-8-azaspiro[4,5]decane

수율 197.8%

용매

ethanol

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled in an ice-water bath
2. 2
   기타removed
3. 3
   workup.DISTILLATIONEthanol was distilled off under reduced pressure
4. 4
   기타the residue was purified by silica gel column chromatography

실험 절차

To a solution of 2,8-dimethyl-1-oxa-8-azaspiro[4,5]-decan-3-one (200 mg) in 7 ml ethanol, was added 25 mg sodium borohydride at room temperature, and the mixture was stirred at room temperature for two hours. The reaction mixture was cooled in an ice-water bath, acidified by addition of 6N-HCl (to about pH 4), and stirred for about 20 minutes with the ice-water bath removed. Ethanol was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography by using, as eluent, a mixed solvent of chloroform/methanol/conc. ammonia (5:1:0.1 by volume), giving 200 mg of 3-hydroxy-2,8-dimethyl-1-oxa-8-azaspiro[4,5]decane as oil. It was dissolved in ether, and ethanolic hydrogen chloride was added to this solution, thus giving its hydrochloride as white crystals.

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