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Sodium periodate → Tert-butyl 2-(4-formyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

HRID 1501813
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1501813
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[CH2:5][CH2:4][N:3]1[C:19]1[CH2:20][O:21][C:22](=[O:26])[C:23]=1[CH:24]=C.I([O-])(=O)(=O)=[O:28].[Na+]>CC(C)=O.O>[CH:24]([C:23]1[C:22](=[O:26])[O:21][CH2:20][C:19]=1[N:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]2)[C:2]1=[O:1])=[O:28]
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Komponenten

5

Edukt 2

HCID 23667635Sodium periodateHCID 86709509Tert-butyl 1-oxo-2-(5-oxo-4-vinyl-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

Produkt 1

HCID 86709510Tert-butyl 2-(4-formyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962
Water
Lösungsmittel

Versuchsvorschrift

tert-butyl 1-oxo-2-(5-oxo-4-vinyl-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate (1.6 g, 4.4 mmol) was dissolved in acetone (36 mL) and water (36 mL), then K2OsO4.2H2O was added and the mixture was stirred for ˜5 min. Solid sodium periodate (3.77 g, 17.6 mmol) was added in 4 portions during 1 hour and the reaction temperature was maintained below 40° C. using an ice-bath. The resulting mixture was stirred for 1 hour at room temperature. LCMS after 2 hours showed complete consumption of starting material. The suspension was filtered and the filtrate was concentrated to remove acetone. The aqueous layer was extracted with DCM (3×). Combined organic layers were washed with 10% Na2S2O3 solution (2×), dried over anhydrous Na2SO4, filtered, concentrated to obtain the title compound, which was taken to the next step without further purification.

Aufarbeitung

  1. temperaturethe reaction temperature was maintained below 40° C.
  2. stirringThe resulting mixture was stirred for 1 hour at room temperature
  3. waitLCMS after 2 hours showed complete
  4. customconsumption of starting material
  5. filtrationThe suspension was filtered
  6. concentrationthe filtrate was concentrated
  7. customto remove acetone
  8. extractionThe aqueous layer was extracted with DCM (3×)
  9. washCombined organic layers were washed with 10% Na2S2O3 solution (2×)
  10. dry with materialdried over anhydrous Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2eb50bb653a94c3dac6064416669f6af
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09206198B2

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