Diisopropylethylamine → 2-Nitro-5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

HRID 449690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449690
Br[CH2:2][CH2:3][N:4]1[C:8]([CH2:9]Br)=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[N:5]1.[O:14]1[CH2:17][CH:16]([NH2:18])[CH2:15]1.C(N(C(C)C)CC)(C)C>C(#N)C>[N+:11]([C:6]1[CH:7]=[C:8]2[CH2:9][N:18]([CH:16]3[CH2:17][O:14][CH2:15]3)[CH2:2][CH2:3][N:4]2[N:5]=1)([O-:13])=[O:12]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 98339233-OxetanamineHCID 575020831-(2-bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole

Produkt 1

HCID 667429562-Nitro-5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazineAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 1-(2-bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole (500 mg, 1.6 mmol) in acetonitrile (20 mL) was added oxetan-3-amine (140 mg, 1.92 mmol) and diisopropylethyl amine (372 mg, 0.50 ml, 2.88 mmol) drop wise and the resulting mixture was stirred at room temperature for 24 h. The solution was concentrated and the residue dissolved in ethyl acetate (50 mL), washed with water (50 mL) and dried over magnesium sulfate. The resulting mixture was filtered and evaporated and the residue purified by flash chromatography (SF25-40 g, 50% to 100% ethyl acetate in hexanes) to give 2-nitro-5-oxetan-3-yl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazine (255 mg, 71%) as a light yellow solid.

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue dissolved in ethyl acetate (50 mL)
  3. washwashed with water (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe resulting mixture was filtered
  6. customevaporated
  7. customthe residue purified by flash chromatography (SF25-40 g, 50% to 100% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-715e76597b2e47b794e2df5ea17d2996
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481540B2

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