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

HRID 245365Notes

Reaction equation

HRID 245365 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[Si:12]([O:29][CH2:30][C:31]1[C:32]([N:47]2[CH2:52][C@H:51]([CH3:53])[O:50][C@H:49]([CH3:54])[CH2:48]2)=[C:33]([F:46])[C:34]([F:45])=[C:35]([CH:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[OH:38])[CH:36]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[Si:12]([O:29][CH2:30][C:31]1[C:32]([N:47]2[CH2:48][C@H:49]([CH3:54])[O:50][C@H:51]([CH3:53])[CH2:52]2)=[C:33]([F:46])[C:34]([F:45])=[C:35]([C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)=[O:38])[CH:36]=1)([C:25]([CH3:26])([CH3:27])[CH3:28])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 86658051{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(pyridin-2-yl)methanol2×HCID 178418287HCID 178418287, compound

Product 1

HCID 86717850{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(pyridin-2-yl)methanone

Procedure

PCC (1.07 g, 0.005 mmol) was added to a solution of {5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(pyridin-2-yl)methanol (Intermediate 18, 1.8 g, 0.002 mmol) in anhydrous DMC (15 mL) at 0° C. and the mixture was allowed to stir for 1 h at room temperature. The reaction mixture was filtered and the solvents were removed under vacuum and the residue was purified over silica gel chromatography column using an ethyl acetate-pet. ether gradient, providing the title compound. Yield: 1.5 g (83%). MS (ES) MH+: 603.2 for C35H40F2N2O3Si

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvents were removed under vacuum
  3. customthe residue was purified over silica gel chromatography column

Sources & evidence

ORD record
ord-e0fe819140894bd787cfc4e2d9bb0ea9
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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