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Sodium Carbonate → 2-(benzyloxy)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one

HRID 571724
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 571724
[CH2:1]([O:8][C:9]1[CH:13]=[C:12](C(OCC)=O)[N:11]([CH2:19][CH2:20][NH:21][C:22]([O:24]C(C)(C)C)=O)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl.O1CCOCC1.O>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]2[C:22](=[O:24])[NH:21][CH2:20][CH2:19][N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 10340Sodium CarbonateHCID 86706489ethyl 3-(benzyloxy)-1-{2-[(tert-butoxycarbonyl)amino]ethyl}-1H-pyrazole-5-carboxylate

Produkt 1

HCID 727147872-(benzyloxy)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-oneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 962Water
Lösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Ethyl 3-(benzyloxy)-1-{2-[(tert-butoxycarbonyl)amino]ethyl}-1H-pyrazole-5-carboxylate (0.51 g, 1.31 mmol) was dissolved in a 4 M solution of HCl in 1,4-dioxane (6.53 mL). The mixture was stirred at room temperature for 1 hour and then basified with a saturated solution of Na2CO3. The mixture was stirred at room temperature for 1 hour, diluted with water and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; 7 M solution of ammonia in MeOH in DCM 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-(benzyloxy)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one (0.31 g, 99% yield) as a white solid.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvents evaporated in vacuo
  7. customThe crude product was purified by flash column chromatography (silica; 7 M solution of ammonia in MeOH in DCM 0/100 to 10/90)
  8. customThe desired fractions were collected
  9. customthe solvents evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8f052d13990e4e9e8476f1d0aa6169ad
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09029366B2

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