StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Potassium Phosphate, Tribasic → Tert-butyl 1-oxo-2-(5-oxo-4-vinyl-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

HRID 1501812
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1501812
Br[C:2]1[C:6](=[O:7])[O:5][CH2:4][C:3]=1[N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[C:9]1=[O:25].[B-](F)(F)(F)[CH:27]=[CH2:28].[K+].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:25]=[C:9]1[C:10]2([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH2:11][CH2:12][N:8]1[C:3]1[CH2:4][O:5][C:6](=[O:7])[C:2]=1[CH:27]=[CH2:28]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 23679353Potassium vinyltrifluoroborateHCID 86709468tert-Butyl 2-(4-bromo-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

tert-butyl 2-(4-bromo-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (2.2 g, 5.30 mmol), potassium trifluoro(vinyl)borate (1.06 g, 7.95 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.345 g, 0.530 mmol) and potassium phosphate tribasic (10.60 mL, 10.60 mmol) were taken up in THF (44.1 mL) in a sealed tube, de-gassed and the resulting mixture was heated overnight at 70° C. The reaction mixture was cooled to room temperature and then was diluted with EtOAc and water. After separation of layers, the aqueous layer was extracted with EtOAc (2×). The combined organic layers were dried over anhydrous MgSO4, filtered, concentrated and purified by silica gel column chromatography using (30-100) % EtOAc/hexanes as mobile phase to provide the title compound.

Aufarbeitung

  1. customde-gassed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additionwas diluted with EtOAc and water
  4. customAfter separation of layers
  5. extractionthe aqueous layer was extracted with EtOAc (2×)
  6. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cb19f948f7e4416ca38569a658209e73
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09206198B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion