Methyl morpholine oxide → HCID 86622960, compound

HRID 1715420Notes

Reaction equation

HRID 1715420 reaction equation
C[N+]1([O-])CCOCC1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][C:19](=[O:25])[CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:12][C:11]=1[CH2:26][OH:27]>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][C:19](=[O:25])[CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:12][C:11]=1[CH:26]=[O:27]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 68503951HCID 68503951, compound

Product 1

HCID 86622960HCID 86622960, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

NMO (318 mg, 2.28 mmol) was added to a sol. of N-[2-(4-chloro-3-hydroxymethyl-phenyl)-ethyl]-3,3,3-trifluoro-propionamide (225 mg, 0.761 mmol) in CH2Cl2 (16 mL). The mixture was stirred for 30 min, and tetrapropylammonium perruthenate (26.7 mg, 0.076 mmol) was added. The mixture was stirred for 1 h at rt, and was filtered over Celite. The filtrate was evaporated under reduced pressure. Purification of the crude by FC (CH2Cl2/MeOH 19:1) yielded the title compound (180 mg, 81%). LC-MS: tR=0.88 min; ES+: 335.28.

Workup

  1. stirringThe mixture was stirred for 1 h at rt
  2. filtrationwas filtered over Celite
  3. customThe filtrate was evaporated under reduced pressure
  4. customPurification of the crude by FC (CH2Cl2/MeOH 19:1)

Sources & evidence

ORD record
ord-a849d5475c444f1097d1d4eb0fd0ef3a
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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