HCID 22645428, compound → HCID 22645396, compound

HRID 2414271Notes

Reaction equation

HRID 2414271 reaction equation
[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:21])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=C)[CH:14]=2)[CH:9]([CH3:22])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].I([O-])(=O)(=O)=[O:24].[Na+]>O.CC(C)=O.[Os](=O)(=O)(=O)=O>[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:21])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[O:24])[CH:14]=2)[CH:9]([CH3:22])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 2

HCID 22645428HCID 22645428, compoundHCID 23667635Sodium periodate

Product 1

HCID 22645396HCID 22645396, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

1-Hexyl-3,4-dimethyl-4-(3-vinylphenyl)piperidine (Example 26, 200 mg, 0.67 mmol) was dissolved in a mixture of water (2 μL) and acetone (18 mL). Osmium tetroxide (200 μL, 2.5% w/w in tert-butanol) was added, followed by sodium periodate (572 mg, 2.68 mmol) which was added portionwise. The reaction mixture was stirred at room temperature for 26 hours, then it was filtered to remove precipitate and the solvent was removed by evaporation in vacuo. The residue was partitioned between dichloromethane (25 mL) and saturated sodium chloride solution (25 mL). The organic phase was separated, dried (Na2SO4) and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel (50 g) eluted with ethyl acetate:hexane:0.880 ammonia (74:25:1). The title compound was obtained as an oil (80 mg).

Workup

  1. additionwas added portionwise
  2. filtrationit was filtered
  3. customto remove precipitate
  4. customthe solvent was removed by evaporation in vacuo
  5. customThe residue was partitioned between dichloromethane (25 mL) and saturated sodium chloride solution (25 mL)
  6. customThe organic phase was separated
  7. dry with materialdried (Na2SO4)
  8. customthe solvent removed in vacuo
  9. customThe residue was purified by column chromatography on silica gel (50 g)
  10. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-cd87ec4c70c54892806809a4a69e0940
Source dataset
uspto-grants-2004_11
Patent number
US06812236B2

Reaction notes

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