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Sodium hydride → 2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate

HRID 856193
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 856193
[H-].[Na+].[F:3][C:4]([F:35])([F:34])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][CH2:20][C:21]([OH:33])([CH3:32])[CH2:22][N:23]3[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[N:25]=[C:24]3Cl)=[O:18])[CH2:15][CH:16]=2)=[CH:7][CH:6]=1>CN(C=O)C>[F:3][C:4]([F:35])([F:34])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][CH2:20][C:21]3([CH3:32])[O:33][C:24]4=[N:25][C:26]([N+:28]([O-:30])=[O:29])=[CH:27][N:23]4[CH2:22]3)=[O:18])[CH2:15][CH:16]=2)=[CH:7][CH:6]=1
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Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 694795953-(2-Chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate

Produkt 1

HCID 230811032-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carboxylateAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

Sodium hydride (11 mg, 0.28 mmol) was added to a solution of 3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate prepared in Example 85 (0.11 g, 0.23 mmol) in DMF (1 ml) followed by stirring for 1 hour with cooling on ice-bath. Ice-water was added to the reaction mixture, the resulting mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=4/1) and then washed with diisopropyl ether to afford 2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate (0.04 g, yield 39%) as a white solid.

Aufarbeitung

  1. temperaturewith cooling on ice-bath
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=4/1)
  7. washwashed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9341152c20c64963b47ec3d733fa5760
Quelldatensatz
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07262212B2

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