Methyl morpholine oxide → HCID 18671473, compound

HRID 1057490Notes

Reaction equation

HRID 1057490 reaction equation
C[N+]1([O-])CC[O:5]CC1.[O:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.O.[C:15]([O:19][C:20]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25](CCC=C)[N:24]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>[Os](=O)(=O)(=O)=O>[OH:5][CH:12]([CH2:13][OH:9])[CH2:11][CH2:10][C:25]1[N:24]=[C:23]([NH:22][C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 21849063HCID 21849063, compoundHCID 21881883Oxolane--water (1/1)

Product 1

HCID 18671473HCID 18671473, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a stirring solution of 4-methylmorpholine N-oxide(2.1 eq) and osmium tetraoxide (2.5 eq) in tetrahydrofuran/water (5 eq/1 eq) was added (tert-butoxy)-N-(6-but-3-enyl(2-pyridyl))carboxamide (1.0 eq) at 25° C. and stirred for 18 hr. The reaction was quenched with solution of sodium bisulfate (0.5M) and sodium sulfite (1M) and stirred for 30 mins. The reaction was poured into a brine and extracted with ethyl acetate. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (50% EtOAc/Hexane). EI-MS m/z 283(M+H)+

Workup

  1. customThe reaction was quenched with solution of sodium bisulfate (0.5M) and sodium sulfite (1M)
  2. stirringstirred for 30 mins
  3. additionThe reaction was poured into a brine
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-ff03347c428c46bb9e951a47643b7dd7
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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