Methyl morpholine oxide → {5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(phenyl)methanone

HRID 245364Notes

Reaction equation

HRID 245364 reaction equation
C[N+]1([O-])CCOCC1.[Si:9]([O:26][CH2:27][C:28]1[C:29]([N:44]2[CH2:49][C@H:48]([CH3:50])[O:47][C@H:46]([CH3:51])[CH2:45]2)=[C:30]([F:43])[C:31]([F:42])=[C:32]([CH:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[OH:35])[CH:33]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl.CC#N.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[Si:9]([O:26][CH2:27][C:28]1[C:29]([N:44]2[CH2:45][C@H:46]([CH3:51])[O:47][C@H:48]([CH3:50])[CH2:49]2)=[C:30]([F:43])[C:31]([F:42])=[C:32]([C:34]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:35])[CH:33]=1)([C:22]([CH3:24])([CH3:23])[CH3:25])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 86658050{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(phenyl)methanol2×

Product 1

HCID 86658052{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(phenyl)methanone

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

NMO (428 mg, 0.0037 mmol) and TPAP (65 mg, 0.0002 mmol) were added to a stirred solution of {5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(phenyl)methanol (Intermediate 17, 1.1 g, 0.002 mmol) in CH2Cl2:CH3CN (1:1, 10 mL) 0° C. The mixture was allowed to warm to room temperature with stirring for 12 hours. The solvents were removed, and the residue was purified over a silica gel chromatography column using an ethyl acetate-pet. ether gradient, providing the title compound. Yield: 1 g, (92%)

Workup

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

Sources & evidence

ORD record
ord-91b0004cf5594e798b719d9770e5bc42
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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