Hydrochloric Acid → 3-Hydroxy-2,8-dimethyl-1-oxa-8-azaspiro[4.5]decane

HRID 36005

반응식

HRID 36005 반응식
[CH3:1][CH:2]1[C:6](=[O:7])[CH2:5][C:4]2([CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)[O:3]1.[BH4-].[Na+].Cl>C(O)C>[NH3:10].[OH:7][CH:6]1[CH2:5][C:4]2([CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)[O:3][CH:2]1[CH3:1]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 101764012,8-Dimethyl-1-oxa-8-azaspiro[4.5]decan-3-one

생성물 2

HCID 222AmmoniaHCID 103975203-Hydroxy-2,8-dimethyl-1-oxa-8-azaspiro[4.5]decane수율 197.8%

시약·촉매·용매 1

HCID 702Ethanol용매

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.

후처리

  1. temperatureThe reaction mixture was cooled in an ice-water bath
  2. customremoved
  3. distillationEthanol was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-0370b22b60c349228458cfb51242cdd1
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05412096

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