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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
Notes
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Reaction equation

HRID 856193 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9341152c20c64963b47ec3d733fa5760
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07262212B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes