Sodium Hydroxide → 2,8-Dimethyl-1-oxa-8-azaspiro[4.5]decan-3-one

HRID 36004

Reaktionsgleichung

Reaktionsgleichung von HRID 36004
[CH3:1][CH:2]1[C:6](=[O:7])[CH:5](C(OCC)=O)[C:4]2([CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[O:3]1.[OH-].[Na+]>Cl>[CH3:1][CH:2]1[C:6](=[O:7])[CH2:5][C:4]2([CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[O:3]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 10377656Ethyl 2,8-dimethyl-3-oxo-1-oxa-8-azaspiro[4,5]decane-4-carboxylate

Produkt 1

HCID 101764012,8-Dimethyl-1-oxa-8-azaspiro[4.5]decan-3-oneAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

Ethyl 2,8-dimethyl-3-oxo-1-oxa-8-azaspiro[4,5]decane-4-carboxylate (3.08 g) was dissolved in 50 ml of 1N-HCl, and the solution was heated under reflux for eight hours. The reaction mixture was allowed to cool to room temperature, then cooled in an ice-water bath, and basified by addition of 20% aqueous solution of caustic soda. This alkaline solution was extracted thrice with about 80 ml of chloroform, and the combined extract was washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. Distilling off the solvent under reduced pressure from the dried solution left 2 g of yellow residue, which was purified by silica gel column chromatography by using, as eluent, a mixed solvent of chloroform/methanol (20:1 by volume), giving 1.8 g of 2,8-dimethyl-1-oxa-8-azaspiro[4,5]decan-3-one as oil. It was dissolved in ether, and ethanolic hydrogen chloride was added, thus giving its hydrochloride as crystals.

Aufarbeitung

  1. temperaturethe solution was heated
  2. temperatureunder reflux for eight hours
  3. temperaturecooled in an ice-water bath
  4. extractionThis alkaline solution was extracted thrice with about 80 ml of chloroform
  5. extractionthe combined extract
  6. washwas washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationDistilling off the solvent under reduced pressure from the dried solution
  9. waitleft 2 g of yellow residue, which
  10. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5d51820b4ad84fd091837bd637b0d5d2
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05412096

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