Methyl morpholine oxide → HCID 86623988, compound

HRID 1426687Notes

Reaction equation

HRID 1426687 reaction equation
[F:1][C:2]1[C:7]([C:8]2[NH:12][CH:11]=[C:10]([CH2:13][OH:14])[C:9]=2[CH3:15])=[CH:6][CH:5]=[CH:4][N:3]=1.C[N+]1([O-])CCOCC1>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]1[C:7]([C:8]2[NH:12][CH:11]=[C:10]([CH:13]=[O:14])[C:9]=2[CH3:15])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 67396611HCID 67396611, compound

Product 1

HCID 86623988HCID 86623988, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of [5-(2-fluoropyridin-3-yl)-4-methyl-1H-pyrrol-3-yl]methanol (1.70 g) in acetonitrile (35 mL) were added tetra-n-propylammonium perruthenate (103 mg), N-methylmorpholine N-oxide (1.44 g) and molecular sieves 4A powder (0.89 g), and the mixture was stirred at room temperature for 2 days. The reaction mixture was filtrated and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:2) to give the title compound as colorless crystals (yield 527 mg, 31%).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:2)

Sources & evidence

ORD record
ord-b1d94c521ab84004816537ae140e2288
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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