Water → HCID 22645419, compound

HRID 2414270Notes

Reaction equation

HRID 2414270 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]=[CH2:20])[CH:14]=2)[CH:9]([CH3:22])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C[N+]1([O-])CC[O:27]CC1.[OH2:31]>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]([OH:27])[CH2:20][OH:31])[CH:14]=2)[CH:9]([CH3:22])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 22645428HCID 22645428, compound

Product 1

HCID 22645419HCID 22645419, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

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 mL) and acetone (18 mL). 4-methylmorpholine N-oxide (172 mg, 1.47 mmol) was added with stirring followed by osmium tetroxide (200 μL, 2.5% w/w in tert-butanol). The reaction mixture was stirred at room temperature for 4 hours before the solvent was removed by evaporation in vacuo. The residue was partitioned between dichloromethane (25 mL) and water (25 mL). The organic phase was separated and dried (Na2SO4). Concentration in vacuo gave a residue which was purified by column chromatography on silica gel (10 g) eluted with a gradient of ethyl acetate:hexane:ammonium hydroxide solution (50:49:1 to 60:33:1), followed by ethyl acetate:methanol:ammonium hydroxide solution (94:5:1). Combination of the appropriate fractions and evaporation to dryness in vacuo gave the product as a yellow oil (145 mg).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 4 hours before the solvent
  2. customwas removed by evaporation in vacuo
  3. customThe residue was partitioned between dichloromethane (25 mL) and water (25 mL)
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentration in vacuo
  7. customgave a residue which
  8. customwas purified by column chromatography on silica gel (10 g)
  9. washeluted with a gradient of ethyl acetate
  10. customCombination of the appropriate fractions and evaporation to dryness in vacuo

Sources & evidence

ORD record
ord-39e0ede68a744241b7f1cacc2864a4db
Source dataset
uspto-grants-2004_11
Patent number
US06812236B2

Reaction notes

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