Methyl morpholine oxide → HCID 86710158, compound

HRID 705384Notes

Reaction equation

HRID 705384 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:18]=[C:17]([N:19]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[S:20]([CH3:23])(=[O:22])=[O:21])[C:16]([O:33][CH:34]([CH3:36])[CH3:35])=[CH:15][C:11]=3[C:12]=2[CH2:13][OH:14])=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:18]=[C:17]([N:19]([CH2:24][C:25]4[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=4)[S:20]([CH3:23])(=[O:22])=[O:21])[C:16]([O:33][CH:34]([CH3:36])[CH3:35])=[CH:15][C:11]=3[C:12]=2[CH:13]=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 86710159HCID 86710159, compound

Product 1

HCID 86710158HCID 86710158, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

N-(2-(4-fluorophenyl)-3-(hydroxymethyl)-5-isopropoxybenzofuran-6-yl)-N-(4-methoxybenzyl)methanesulfonamide (0.68 g, 1.32 mmol) was dissolved in dichloromethane. N-methyl morpholine oxide (0.23 g, 1.99 mmol), 4 A molecular sieves (0.7 g) and finally tetrapropylammonium perruthenate (0.023 g, 0.066 mmol) were added. The resulting black slurry was stirred for 60 minutes at room temperature. The reaction mixture was filtered through a pad of diatomaceous earth, and the solid was washed with dichloromethane until the washes were clear. The combined dichloromethane washes were applied to a dry 10 g silica gel cartridge and the column was eluted with ethyl acetate until no more product was eluted. The solvent was removed in vacuo leaving a tan solid, 0.65 g, 96%.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. washthe solid was washed with dichloromethane until the washes
  3. washthe column was eluted with ethyl acetate until no more product
  4. washwas eluted
  5. customThe solvent was removed in vacuo
  6. customleaving a tan solid, 0.65 g, 96%

Sources & evidence

ORD record
ord-4be6eabe62f6478592d02dc06b667119
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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