Methyl morpholine oxide → HCID 85908183, compound

HRID 2116459Notes

Reaction equation

HRID 2116459 reaction equation
[CH2:1]([C:4]1[C:5]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[N:6][C:7]([Cl:11])=[N:8][C:9]=1[Cl:10])[CH:2]=C.C[N+]1([O-])CC[O:24]CC1>ClCCl.[Os](=O)(=O)(=O)=O>[Cl:11][C:7]1[N:8]=[C:9]([Cl:10])[C:4]([CH2:1][CH:2]=[O:24])=[C:5]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:6]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 85908181HCID 85908181, compound

Product 1

HCID 85908183HCID 85908183, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product from step (i) (2 g) in dichloromethane (40 ml) was added to a solution of osmium tetroxide (1 ml, 2.5% wt in isopropylalcohol) and 4-methylmorpholine N-oxide (1.12 g) in dichloromethane (1 ml). After stirring at room temperature for 24 h the mixture was washed with water, aqueous sodium sulphite solution, dried (MgSO4) and evaporated under reduced pressure. The residue was dissolved in methanol (40 ml), cooled to 0° C. and lead tetraacetate (3.85 g) added. After 1 h the mixture was diluted with water, extracted with ethyl acetate, the organics dried (MgSO4) and evaporated under reduced pressure. Yield 2 g

Workup

  1. washwas washed with water, aqueous sodium sulphite solution
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in methanol (40 ml)
  5. temperaturecooled to 0° C.
  6. additionlead tetraacetate (3.85 g) added
  7. additionAfter 1 h the mixture was diluted with water
  8. extractionextracted with ethyl acetate
  9. dry with materialthe organics dried (MgSO4)
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7bcfe4fc46ea40af8ca6dc02967154da
Source dataset
uspto-grants-2008_10
Patent number
US07439240B2

Reaction notes

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