Isopropanol → trans-2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropanecarbaldehyde

HRID 1639754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639754
[CH3:1][C:2]1[CH:15]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[CH2:13][OH:14])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.C[N+]1([O-])CCOCC1.CC(O)C>C(#N)C.C(OCC)(=O)C>[CH3:1][C:2]1[CH:15]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[CH:13]=[O:14])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Komponenten

6

Edukt 3

HCID 3776IsopropanolHCID 82029Methyl morpholine oxideHCID 66720627Trans-[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanol

Produkt 1

HCID 86641921trans-2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropanecarbaldehydeAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Trans-[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanol (2000 mg, 9.89 mmol), 4 Å molecular sieves (800 mg), 4-methylmorpholine N-oxide (1.74 g, 14.8 mmol) and tetra-n-propylammonium perruthenate(VII) (174 mg, 0.494 mmol) were dissolved in acetonitrile (100 mL), and the mixture was stirred at room temperature for 2 hr. 2-Propanol was added and the mixture was stirred for 30 min, diluted with ethyl acetate, and washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (1.62 g, yield 82%).

Aufarbeitung

  1. stirringthe mixture was stirred for 30 min
  2. washwashed with water and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-b00a67482dc14228a427cada17e7c6b5
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110585B2

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