Methyl morpholine oxide → HCID 86722039, compound

HRID 525021Notes

Reaction equation

HRID 525021 reaction equation
[C:1]1([S:7]([N:10]2[CH:14]=[CH:13][C:12]([CH:15]=C)=[C:11]2[C:17]([O:19][CH3:20])=[O:18])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+]1([O-])CC[O:25]CC1.I([O-])(=O)(=O)=O.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.[Os](=O)(=O)(=O)=O.O>[CH:15]([C:12]1[CH:13]=[CH:14][N:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[C:11]=1[C:17]([O:19][CH3:20])=[O:18])=[O:25]

Participants

8

Reactant 4

HCID 82029Methyl morpholine oxideHCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 86722040HCID 86722040, compound

Product 1

HCID 86722039HCID 86722039, compoundYield 88.4%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 1-(phenylsulfonyl)-3-vinyl-1H-pyrrole-2-carboxylate (1640 mg, 5.63 mmol) in 45 ml of tetrahydrofurane were added 4-methylmorpholine 4-oxide (1.36 g, 11.3 mmol) and 2,4 ml (0.39 mmol) of a 4% aqueous solution of osmium tetraoxide and the reaction was leaved with stirring at room temperature overnight. Afterwards, the starting material was completely consumed and the reaction mixture was filtered through a pad of Celite® using tetrahydrofurane. The filtrate was evaporated to dryness, taken up with ethyl acetate and washed with water and brine. The organic layer was dried (Na2SO4) and concentrated to give a brown residue that was immediately submitted to the next step. In this sense, this residue was dissolved in tetrahydrofurane (28 ml) and water (3,4 ml) and solid sodium periodate (1.8 g, 8.4 mmol) was added stirring the reaction vigorously at room temperature overnight. Next day, a suspension was formed and reaction was finished. The work-up was done by adding 4% aqueous solution of sodium bicarbonate (200 ml) and extracting with ethyl acetate (3×). The organic mixture was washed with water and brine, dried (Na2SO4) and concentrated to dryness to give a residue that was purified by flash chromatography silica (hexane/ethyl acetate) to give a 1.46 g (88% yield) of the title compound.

Workup

  1. customthe reaction was leaved
  2. customAfterwards, the starting material was completely consumed
  3. filtrationthe reaction mixture was filtered through a pad of Celite®
  4. customThe filtrate was evaporated to dryness
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated
  8. customto give a brown residue that
  9. stirringstirring
  10. customthe reaction vigorously at room temperature overnight
  11. customNext day, a suspension was formed
  12. customreaction
  13. extractionextracting with ethyl acetate (3×)
  14. washThe organic mixture was washed with water and brine
  15. dry with materialdried (Na2SO4)
  16. concentrationconcentrated to dryness
  17. customto give a residue that
  18. customwas purified by flash chromatography silica (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b440b1249cda42bfa3afb8f6068fb6fa
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

Loading…