Water → HCID 69481645, compound

HRID 856270Notes

Reaction equation

HRID 856270 reaction equation
Cl[C:2]1[N:3]([CH2:10][C@@:11]([CH3:32])([OH:31])[CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)[CH2:15][CH2:14]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+].O>CN(C=O)C>[CH3:32][C@@:11]1([CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)[CH2:15][CH2:14]2)[O:31][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 69479606HCID 69479606, compound

Product 1

HCID 69481645HCID 69481645, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-1-(2-Chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(4-trifluoromethylbenzyloxy)piperidin-1-yl]propan-2-ol prepared in Example 254 (1.36 g, 2.8 mmol) was dissolved in DMF (15 ml). To the solution, sodium hydride (134 mg, 3.36 mmol) was added with cooling on ice-bath followed by stirring at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with a saturated saline solution, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=10/1) and crystallized from methylene chloride-diisopropyl ether to afford (S)-2-methyl-6-nitro-2-[4-(4-trifluoromethylbenzyloxy)piperidin-1-ylmethyl]-2,3-dihydroimidazo[2,1-b]oxazole (431 mg, yield 44%) as a white powder.

Workup

  1. temperaturewith cooling on ice-bath
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with a saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=10/1)
  8. customcrystallized from methylene chloride-diisopropyl ether

Sources & evidence

ORD record
ord-20e39c9ab74f4ccebdff787136b33f8b
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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