Ethylene Glycol → 1,4-Dioxa-7-azaspiro[4.5]decane

HRID 1693403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1693403
C([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]1)(OC(C)(C)C)=O.[CH2:15](O)[CH2:16][OH:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[O:14]1[C:10]2([CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)[O:17][CH2:16][CH2:15]1

Komponenten

6

Edukt 4

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylate

Produkt 1

HCID 123947731,4-Dioxa-7-azaspiro[4.5]decane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 1-Boc-3-piperidone (700 mg, 3.51 mmol) in toluene (20 mL) was added ethylene glycol (588 μL, 10.54 mmol) followed by p-toluene sulfonic acid hydrate (1.0 g, 5.27 mmol) and the reaction heated to reflux using Dean-Stark apparatus for 7 h. To the mixture was added NaHCO3 solution, and the organic layer was removed. The aqueous phase was evaporated to dryness and the resulting residue dissolved in THF. Filtration through celite and removal of the solvent in vacuo gave the desired product as light brown oil. δH (CD3OD): 3.99 (2H, s), 3.73-3.57 (2H, m), 3.63 (4H, m), 2.77 (1H, m), 2.73 (1H, m), 1.76 (2H, m).

Aufarbeitung

  1. temperaturethe reaction heated
  2. temperatureto reflux
  3. customfor 7 h
  4. customthe organic layer was removed
  5. customThe aqueous phase was evaporated to dryness
  6. dissolutionthe resulting residue dissolved in THF
  7. filtrationFiltration
  8. customthrough celite and removal of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f337735af8c9448fa14e12cef9ccaf60
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158622B2

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