Dimethyl Sulfoxide → Benzyl 4-(oxiran-2-ylmethoxy)piperidine-1-carboxylate

HRID 2368105Notes

Reaction equation

HRID 2368105 reaction equation
[I-].C[S+](C)(C)=O.[H-].[Na+].[CH3:9]S(C)=O.[O:13]=[CH:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:19][CH2:18]1>O>[O:13]1[CH2:9][CH:14]1[CH2:15][O:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 57517496Benzyl 4-(2-oxoethoxy)piperidine-1-carboxylate

Product 1

HCID 57517497Benzyl 4-(oxiran-2-ylmethoxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of trimethylsulfoxonium iodide (2.17 g), sodium hydride (oil, 60%, 395 mg) and dimethyl sulfoxide (20 mL) was stirred at room temperature for 1 hr, and benzyl 4-(2-oxoethoxy)piperidine-1-carboxylate (2.28 g) was added thereto. The obtained mixture was stirred at room temperature for 3 days. Water was added thereto, and the obtained mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (208 mg).

Workup

  1. stirringThe obtained mixture was stirred at room temperature for 3 days
  2. extractionthe obtained mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-01546043d50c4dd69623995b65c502da
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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