Water → HCID 69481530, compound

HRID 856272Notes

Reaction equation

HRID 856272 reaction equation
Cl[C:2]1[N:3]([CH2:10][C@@:11]([CH3:26])([OH:25])[CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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>[CH3:26][C@@:11]1([CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[O:25][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 69479831HCID 69479831, compound

Product 1

HCID 69481530HCID 69481530, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-1-(2-Chloro-4-nitro-imidazol-1-yl)-2-methyl-3-(4-phenylpiperidin-1-yl)propan-2-ol prepared in Example 276 (0.703 g, 1.86 mmol) was dissolved in DMF (5 ml). To the solution, sodium hydride (89 mg, 2.23 mmol) was added with cooling on ice-bath followed by stirring at room temperature for 3 hours. To the reaction mixture, water was added. The precipitates were filtered off, purified by silica gel column chromatography (n-hexane/acetone=3/1) and recrystallized from ethyl acetate to afford (S)-2-methyl-6-nitro-2-(4-phenylpiperidin-1-ylmethyl)-2,3-dihydroimidazo[2,1-b]oxazole (0.230 g, yield 36%) as a white powder.

Workup

  1. temperaturewith cooling on ice-bath
  2. filtrationThe precipitates were filtered off
  3. custompurified by silica gel column chromatography (n-hexane/acetone=3/1)
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-67bbc0a0cdd14697978b19598fae4045
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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