Methyl morpholine oxide → 2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3,4-difluoro-5-(phenylcarbonyl)benzaldehyde

HRID 245367Notes

Reaction equation

HRID 245367 reaction equation
C[N+]1([O-])CCOCC1.[CH3:9][C@H:10]1[O:15][C@@H:14]([CH3:16])[CH2:13][N:12]([C:17]2[C:22]([CH2:23][OH:24])=[CH:21][C:20]([C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:26])=[C:19]([F:33])[C:18]=2[F:34])[CH2:11]1>C(Cl)Cl.CC#N.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:16][C@H:14]1[O:15][C@@H:10]([CH3:9])[CH2:11][N:12]([C:17]2[C:18]([F:34])=[C:19]([F:33])[C:20]([C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:26])=[CH:21][C:22]=2[CH:23]=[O:24])[CH2:13]1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 86658053{4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluoro-5-(hydroxymethyl)phenyl}(phenyl)methanone2×

Product 1

HCID 866580542-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3,4-difluoro-5-(phenylcarbonyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

NMO (295 mg, 0.0025 mmol) and TPAP (44 mg, 0.0001 mmol) were added to a stirred solution of {4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluoro-5-(hydroxymethyl)phenyl}(phenyl)methanone (Intermediate 23, 450 mg, 0.001 mmol) in anhydrous CH2Cl2:CH3CN (1:1, 10 mL) at 0° C., and the mixture was stirred for 12 hours with warming to room temperature. The solvents were removed and the residue was purified over a silica gel chromatography column using ethyl acetate-pet. ether gradient, providing the title compound. Yield: 340 mg, (76%)

Workup

  1. customThe solvents were removed
  2. customthe residue was purified over a silica gel chromatography column

Sources & evidence

ORD record
ord-3ae3620a29954a8d9162eb89fc64fd70
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

Loading…