Reacción #64283

Ecuación de reacción

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

Rendimiento 197.8%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente