Diethyl Ether → HCID 58573429, compound

HRID 932293Notes

Reaction equation

HRID 932293 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH2:7]([C@@:10]1([CH3:31])[CH2:15][C@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[C@@H:13]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[NH:12][C:11]1=[O:30])[CH:8]=C.C[Si](C=[N+]=[N-])(C)C.C([O:41][CH2:42]C)C>C(#N)C.C(OCC)(=O)C.O.O.[Ru](Cl)(Cl)Cl>[Cl:22][C:18]1[CH:17]=[C:16]([C@@H:14]2[C@@H:13]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[NH:12][C:11](=[O:30])[C@:10]([CH2:7][C:8]([O:41][CH3:42])=[O:2])([CH3:31])[CH2:15]2)[CH:21]=[CH:20][CH:19]=1

Participants

9

Reactant 4

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 23667635Sodium periodateHCID 58574008(3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methylpiperidin-2-one

Product 1

HCID 58573429HCID 58573429, compound

Reagents, catalysts & solvents 4

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium periodate (21.03 g, 98 mmol) was added slowly to a solution containing ruthenium(III) chloride hydrate (0.277 g, 1.229 mmol) and (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methylpiperidin-2-one (4.6 g, 12.29 mmol; Example 71, step D) in acetonitrile (35.1 mL), ethyl acetate (35.1 mL) and water (52.7 mL) while maintaining a temperature below 20° C. The resulting mixture was then stirred for 2 h at room temperature. Next, the reaction was filtered and concentrated, and the resulting residue was further processed by dissolving in ethyl acetate. The organics were washed with water and brine, dried over MgSO4, filtered and concentrated. Next, the residue was dissolved in a small amount of a mixture of ether and methanol (1:1) and a 2M solution of (trimethylsilyl)diazomethane in diethyl ether (12.29 ml, 24.58 mmol) was added. This solution was then allowed to stir at ambient temperature overnight. The solution was concentrated and the resulting residue was purified on silica gel (eluent: hexane/ethyl acetate 0 to 100%, gradient elution) to give the title compound.

Workup

  1. temperaturewhile maintaining a temperature below 20° C
  2. filtrationNext, the reaction was filtered
  3. concentrationconcentrated
  4. dissolutionby dissolving in ethyl acetate
  5. washThe organics were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dissolutionNext, the residue was dissolved in a small amount of a mixture of ether and methanol (1:1)
  10. stirringto stir at ambient temperature overnight
  11. concentrationThe solution was concentrated
  12. customthe resulting residue was purified on silica gel (eluent: hexane/ethyl acetate 0 to 100%, gradient elution)

Sources & evidence

ORD record
ord-5f698f0b991b4f30aed3d35647f2a93c
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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