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Trifluoroacetic acid → Rac-2-phenoxymethyl-4-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazine

HRID 1773795
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1773795
[F:1][C:2]([F:7])([F:6])[C:3](O)=O.[O:8]([CH2:15][C:16]1[CH:24]=[C:19]2C=[N:21][CH2:22][CH2:23][N:18]2[N:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.F.[K].C[Si](C(F)(F)F)(C)C.C([O-])([O-])=O.[Na+].[Na+]>CC#N.CN(C=O)C.O>[O:8]([CH2:15][C:16]1[CH:24]=[C:19]2[CH:3]([C:2]([F:7])([F:6])[F:1])[NH:21][CH2:22][CH2:23][N:18]2[N:17]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 53443437Potassium fluoride, 99%, spray-driedHCID 679583882-Phenoxymethyl-6,7-dihydro-pyrazolo[1,5-a]pyrazine

Produkt 1

HCID 67960098
Rac-2-phenoxymethyl-4-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazine
Ausbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Trifluoroacetic acid (0.36 mL) was added to a stirred mixture of 2-phenoxymethyl-6,7-dihydro-pyrazolo[1,5-a]pyrazine (0.43 g, 1.87 mmol) and potassium hydrogen fluoride (0.18 g, 2.34 mmol) in CH3CN (3.7 mL) and DMF (0.4 mL) at 0° C. The mixture was stirred at 0° C. for 5 minutes. Then Ruppert's reagent (0.83 mL, 5.61 mmol) was added and the mixture was stirred at room temperature for 16 hours. The mixture was treated with a saturated solution of Na2CO3, 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; 7N solution of ammonia in methanol in DCM 0/100 to 30/70). The desired fractions were collected and the solvents evaporated in vacuo to yield rac-2-phenoxymethyl-4-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazine (350 mg, 63% yield) as a yellow oil.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 16 hours
  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; 7N solution of ammonia in methanol in DCM 0/100 to 30/70)
  8. customThe desired fractions were collected
  9. customthe solvents evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-66d36fc6448a4a448226e3ecb7972b0f
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09255103B2

Notizen zur Reaktion

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