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

HRID 856208Notes

Reaction equation

HRID 856208 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][C@@:19]([OH:31])([CH3:30])[CH2:20][N:21]3[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[N:23]=[C:22]3Cl)=[O:16])[CH2:13][CH:14]=2)=[CH:5][CH:4]=1.[H-].[Na+]>CN(C=O)C>[F:1][C:2]([F:33])([F:32])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][C@:19]3([CH3:30])[O:31][C:22]4=[N:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][N:21]4[CH2:20]3)=[O:16])[CH2:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69479590(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 69479770(R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carboxylateYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate prepared in Example 106 (0.32 g, 0.65 mmol) in DMF (3 ml), sodium hydride (31 mg, 0.78 mmol) was added followed by stirring for 1.5 hours with cooling on ice-bath. To the reaction mixture, ice-water was added, and the solution was extracted with ethyl acetate. The organic phase 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=9/1) and recrystallized from isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate (0.14 g, yield 49%) as a white solid.

Workup

  1. temperaturewith cooling on ice-bath
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic phase 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=9/1)
  7. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-e7858dd77c964c1abdb7c0d2d666e606
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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