Sodium hydride → HCID 86673577, compound

HRID 455282Notes

Reaction equation

HRID 455282 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[F:9][C:10]([F:30])([F:29])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:23][C@@H:22]3[CH2:24][C:25](=[O:27])[CH2:26][N:21]3[C:20]2=[O:28])=[CH:15][CH:14]=1>CS(C)=O.[Cl-].[Na+].O>[F:30][C:10]([F:9])([F:29])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:23][C@@H:22]3[CH2:24][C@:25]4([CH2:2][O:27]4)[CH2:26][N:21]3[C:20]2=[O:28])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 70976192HCID 70976192, compound

Product 1

HCID 86673577HCID 86673577, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of trimethyl sulfoxonium iodide (70 mg, 0.350 mmol) and NaH (20 mg, 0.477 mmol), was added dry DMSO (0.3 mL) drop wise at 0° C. and stirred for 30 min. (S)-2-[4-(2,2,2-Trifluoro-ethoxy)-phenyl]-tetrahydro-pyrrolo[1,2-c]imidazole-3,6-dione (100 mg, 0.318 mmol) dissolved in DMSO (0.6 mL) was added to this mixture and stirred at room temperature for 2 h. The reaction mixture was poured into brine and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated. The residue was purified through column chromatography over silica (elution with 30% ethyl acetate in hexane) to obtain 20 mg of isomer (2R,7a′S)-2′-[4-(2,2,2-trifluoroethoxy)phenyl]tetrahydro-3′H-spiro[oxirane-2,6′-pyrrolo[1,2-c]imidazol]-3′-one (off white solid) LC-MS: 329.0 [M+1]+ and 5 mg of isomer (2S,7a′S)-2′-[4-(2,2,2-trifluoroethoxy)phenyl]tetrahydro-3′H-spiro[oxirane-2,6′-pyrrolo[1,2-c]imidazol]-3′-one (off white solid) LC-MS: 329.0 [M+1]+.

Workup

  1. additionwas added to this mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified through column chromatography over silica (elution with 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c7be4c279a3b4d70aa7a9677bf5e59cd
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

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