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

HRID 982331

Reaktionsgleichung

Reaktionsgleichung von HRID 982331
[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]

Komponenten

6

Edukt 3

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

Produkt 2

HCID 222AmmoniaHCID 103975203-Hydroxy-2,8-dimethyl-1-oxa-8-azaspiro[4.5]decaneAusbeute 197,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f0ae5c93ab4c4b65bec3765e2cf0f5f8
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04996210

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