Dimethyl Sulfoxide → 4-Benzyl-2-(2-phenyloxiran-2-yl)morpholine

HRID 899094Notes

Reaction equation

HRID 899094 reaction equation
[I-].C[S+](C)(C)=O.[H-].[Na+].[CH3:9]S(C)=O.[CH2:13]([N:20]1[CH2:25][CH2:24][O:23][CH:22]([C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:27])[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O.O>[CH2:13]([N:20]1[CH2:25][CH2:24][O:23][CH:22]([C:26]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:9][O:27]2)[CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 179717622-Benzoyl-4-benzylmorpholine

Product 1

HCID 596936444-Benzyl-2-(2-phenyloxiran-2-yl)morpholineYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of trimethylsulfoxonium iodide (783 mg, 1 equiv.) and sodium hydride (142 mg, 1 equiv.) in dimethylformamide (17 mL) at 0° C. under nitrogen atmosphere was added dimethylsulfoxide (251 μL, 1 equiv.) and the resulting suspension was stirred for 30 minutes. A solution of (4-Benzyl-morpholin-2-yl)-phenyl-methanone (1 g, 1 equiv.) in dimethylformamide (10 mL) was then added dropwise. Stirring was continued for 30 minutes and the reaction was stopped by addition of water (50 mL). The aqueous solution was extracted with diethyl ether, the organic phase dried with MgSO4, and evaporated in vacuo. The crude material was purified using a column chromatography on silica gel eluting with a mixture of ethyl acetate/heptane (20/80) to give 825 mg of the title compound as a colourless oil (78%), mixture of two diastereoisomers. LCMS (6 minute method) [M+H]+=296 @ Rt 1.88 min. single peak.

Workup

  1. stirringStirring
  2. waitwas continued for 30 minutes
  3. extractionThe aqueous solution was extracted with diethyl ether
  4. dry with materialthe organic phase dried with MgSO4
  5. customevaporated in vacuo
  6. customThe crude material was purified
  7. additionwith a mixture of ethyl acetate/heptane (20/80)
  8. customto give

Sources & evidence

ORD record
ord-2215f9a1a0b74102948885b8943b039d
Source dataset
uspto-grants-2008_04
Patent number
US07354920B2

Reaction notes

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