Water → HCID 22645411, compound

HRID 2414279Notes

Reaction equation

HRID 2414279 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:22])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=C)[CH:15]=2)[CH:10]([CH3:23])[CH2:9]1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O.C[N+]1([O-])CC[O:29]CC1.I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.[Os](=O)(=O)(=O)=O>[C:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:22])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=[O:29])[CH:15]=2)[CH:10]([CH3:23])[CH2:9]1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 22645397HCID 22645397, compoundHCID 23667635Sodium periodate

Product 1

HCID 22645411HCID 22645411, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of 1-hexanoyl-3,4-dimethyl-4-(3-vinylphenyl)piperidine (Preparation 8, 2.4 g, 7.67 mmol) in acetone (20 mL) at room temperature was added water (5 mL), 4-methylmorpholine N-oxide (1.1 g, 9.20 mmol) and finally osmium tetroxide (3.83 mL, 2.5 wt % solution in tert-butanol). The yellow solution was stirred at room temperature for 1 hour and then sodium periodate (4.92 g, 23.0 mmol) was added in one portion. After stirring the reaction for 3 hours a heavy precipitate had developed and the reaction mixture was filtered through Celite®, washing with acetone. The filtrate was concentrated in vacuo, the crude oil was dissolved in dichloromethane, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate:hexane (1:1). The title compound was isolated as clear oil (2.0 g).

Workup

  1. stirringAfter stirring
  2. customthe reaction for 3 hours a heavy precipitate
  3. filtrationthe reaction mixture was filtered through Celite®
  4. washwashing with acetone
  5. concentrationThe filtrate was concentrated in vacuo
  6. dissolutionthe crude oil was dissolved in dichloromethane
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate:hexane (1:1)

Sources & evidence

ORD record
ord-8496b8cb1d92465ead4847a358c52cd5
Source dataset
uspto-grants-2004_11
Patent number
US06812236B2

Reaction notes

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