Methyl morpholine oxide → HCID 58938628, compound

HRID 598101Notes

Reaction equation

HRID 598101 reaction equation
[CH2:1]([N:4]([CH2:27][CH2:28][CH3:29])[C:5]1[CH:6]=[C:7]([CH2:25][OH:26])[C:8](=[O:24])[N:9]2[C:14]=1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=1[CH3:23])[CH2:2][CH3:3].C[N+]1([O-])CCOCC1>ClCCl.C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:27]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]1[CH:6]=[C:7]([CH:25]=[O:26])[C:8](=[O:24])[N:9]2[C:14]=1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]1[C:16]([CH3:23])=[CH:17][C:18]([CH3:22])=[CH:19][C:20]=1[CH3:21])[CH2:28][CH3:29]

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxideHCID 58938660HCID 58938660, compound

Product 1

HCID 58938628HCID 58938628, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

1-(Dipropylamino)-3-(hydroxymethyl)-6-mesityl-4H-quinolizin-4-one (0.60 g, 1.53 mmol) was dissolved in dichloromethane (20 mL) and acetonitrile (4 mL). 0.5 g of crushed sieves (4 angstroms) was added followed by N-methylmorpholine N-oxide (NMO) (0.27 g, 2.3 mmol). Tetrapropylammonium perruthenate (TPAP) (0.081 g, 0.23 mmol) was added last. The reaction stirred for 0.5 h. The solution was filtered and concentrated. Flash chromatography (20% ethyl acetate/hexanes) gave 0.436 g (73% yield) of the title compound as a red solid.

Workup

  1. addition0.5 g of crushed sieves (4 angstroms) was added
  2. filtrationThe solution was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d93215ba11094e5ca9a826a30aa811cb
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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