Sodium periodate → 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxo-1-(pyrimidin-4-yl)piperidin-3-yl)acetaldehyde

HRID 1048332Notes

Reaction equation

HRID 1048332 reaction equation
[CH2:1]([C@@:4]1([CH3:31])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][N:25]=2)[C:5]1=[O:30])[CH:2]=C.I([O-])(=O)(=O)=[O:33].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[Cl:16][C:12]1[CH:11]=[C:10]([C@@H:8]2[C@@H:7]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[N:6]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][N:25]=3)[C:5](=[O:30])[C@:4]([CH2:1][CH:2]=[O:33])([CH3:31])[CH2:9]2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 68000187(3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-(pyrimidin-4-yl)piperidin-2-one

Product 1

HCID 866607212-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxo-1-(pyrimidin-4-yl)piperidin-3-yl)acetaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-(pyrimidin-4-yl)piperidin-2-one (Example 110, Step B) (60 mg, 0.13 mmol) in a mixture of tetrahydrofuran (2.7 mL) and water (880 μL) was added osmium tetroxide (1.7 mg, 6.6 μmol). After 5 minutes, sodium periodate (89 mg, 0.46 mmol) was added and the reaction mixture was stirred for 14 hours. The reaction mixture was filtered through Celite® (J.T. Baker, Phillipsberg, N.J., diatomaceous earth) and washed with EtOAc and water. The organic layer was washed with sat. aq. NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. Purification of the residue by flash chromatography (0 to 75% EtOAc/hexanes, gradient elution) provided the title compound as a colorless solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite® (J.T. Baker, Phillipsberg, N.J., diatomaceous earth)
  2. washwashed with EtOAc and water
  3. washThe organic layer was washed with sat. aq. NaCl solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customPurification of the residue
  8. washby flash chromatography (0 to 75% EtOAc/hexanes, gradient elution)

Sources & evidence

ORD record
ord-ec1182cec5ee420e91e165bcb7a9ead8
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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