Water → HCID 56591284, compound

HRID 932028Notes

Reaction equation

HRID 932028 reaction equation
C([C@@:4]1([CH3:32])[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]=[C:28]([CH3:30])[CH:27]=[CH:26][N:25]=2)[C:5]1=[O:31])C=C.O.C[N+]1([O-])CC[O:38]CC1.C[C:43]([CH3:45])=[O:44].OS(O)(=O)=O.O=[Cr](=O)=O>O1CCCC1.[Os](=O)(=O)(=O)=O.CC(O)(C)C>[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]=[C:28]([CH3:30])[CH:27]=[CH:26][N:25]=3)[C:5](=[O:31])[C@:4]([CH2:45][C:43]([OH:38])=[O:44])([CH3:32])[CH2:9]2)[CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 58573815HCID 58573815, compoundHCID 131709961Jones' reagent

Product 1

HCID 56591284HCID 56591284, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-(4-methylpyridin-2-yl)piperidin-2-one (Example 114, Step A) (73 mg, 0.16 mmol) in 780 μL of tetrahydrofuran was added water (1.0 mL), followed by 2-methylpropan-2-ol (100 μL) at room temperature. The reaction mixture was treated with 4-methylmorpholine 4-oxide (28 mg, 0.24 mmol), followed by osmium tetroxide (2.0 mg, 7.8 μmol) and was stirred at room temperature for 2 hours. The reaction mixture was treated with a 1.25 M solution of Jones reagent (190 μL, 0.24 mmol) at room temperature and was stirred at room temperature for 1 hour. The reaction was quenched with water and extracted (3×EtOAc). The combined organic layers were washed with sat. aq. NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. Purification of the residue by HPLC on an Eclipse column (Agilent Technologies, Santa, Clara, Calif.) (20 to 80% acetonitrile/water, gradient elution) provided the title compound as a colorless solid.

Workup

  1. stirringwas stirred at room temperature for 1 hour
  2. customThe reaction was quenched with water
  3. extractionextracted (3×EtOAc)
  4. washThe combined organic layers were washed with sat. aq. NaCl solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customPurification of the residue by HPLC
  9. washon an Eclipse column (Agilent Technologies, Santa, Clara, Calif.) (20 to 80% acetonitrile/water, gradient elution)

Sources & evidence

ORD record
ord-77cc386a41864244964fc8b1c1098aea
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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