Methyl morpholine oxide → HCID 68668307, compound

HRID 216389Notes

Reaction equation

HRID 216389 reaction equation
C[N+]1([O-])CC[O:5]CC1.[CH3:9][C:10]([CH3:57])([CH:55]=[CH2:56])[CH2:11][C:12]1[N:13]=[C:14]([CH2:36][C:37]([C:42]2[CH:47]=[CH:46][C:45]([C:48]3[CH:53]=[CH:52][C:51]([F:54])=[CH:50][N:49]=3)=[CH:44][CH:43]=2)([OH:41])[CH:38]([F:40])[F:39])[N:15]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=1.CC(C)=O.[OH2:62]>[Os](=O)(=O)(=O)=O>[F:39][CH:38]([F:40])[C:37]([C:42]1[CH:43]=[CH:44][C:45]([C:48]2[CH:53]=[CH:52][C:51]([F:54])=[CH:50][N:49]=2)=[CH:46][CH:47]=1)([OH:41])[CH2:36][C:14]1[N:15]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=[C:12]([CH2:11][C:10]([CH3:57])([CH3:9])[CH:55]([OH:5])[CH2:56][OH:62])[N:13]=1

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 18366337Propan-2-one--water (1/1)HCID 68667693HCID 68667693, compound

Product 1

HCID 68668307HCID 68668307, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

NMO (214 mg, 1.8 mmol) followed by osmium tetroxide (2.5 wt % in n-butanol) (cat.) were added to a solution of 3-[4-(2,2-dimethylbut-3-en-1-yl)-1-trityl-1H-imidazol-2-yl]-1,1-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]propan-2-ol (600 mg, 0.91 mmol) in acetone/water (2:1) (12 mL). After stirring at ambient temperature overnight, the reaction mixture was quenched with saturated aqueous sodium thiosulfate and extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% ethyl acetate/hexane afforded 4-(2-{3,3-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-2-hydroxypropyl}-1-trityl-1H-imidazol-4-yl)-3,3-dimethylbutane-1,2-diol.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium thiosulfate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-248da3f6181e46c894ab42b5f58abed6
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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