Ethyl Acetate → 2-((3R,5R,6S)-5-(3-Chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-cyclopropyl-1-oxobutan-2-yl)-3-methyl-2-oxopiperidin-3-yl)acetic acid

HRID 932280Notes

Reaction equation

HRID 932280 reaction equation
[CH2:1]([C@@:4]1(C)[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@@H:24]([CH2:30][CH3:31])[CH:25]([CH:27]2[CH2:29][CH2:28]2)[OH:26])[C:5]1=[O:32])C=C.I([O-])(=O)(=O)=O.[Na+].CC[O:42][C:43]([CH3:45])=[O:44]>C(#N)C.O.O.[Ru](Cl)(Cl)Cl>[Cl:16][C:12]1[CH:11]=[C:10]([C@@H:8]2[C@@H:7]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[N:6]([C@@H:24]([CH2:30][CH3:31])[C:25]([CH:27]3[CH2:28][CH2:29]3)=[O:26])[C:5](=[O:32])[C@:4]([CH2:45][C:43]([OH:42])=[O:44])([CH3:1])[CH2:9]2)[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 58573334HCID 58573334, compound

Product 1

HCID 585732692-((3R,5R,6S)-5-(3-Chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-cyclopropyl-1-oxobutan-2-yl)-3-methyl-2-oxopiperidin-3-yl)acetic acid

Reagents, catalysts & solvents 3

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((2S)-1-cyclopropyl-1-hydroxybutan-2-yl)-3-methylpiperidin-2-one (Example 417, Step A; 60 mg, 0.123 mmol) in EtOAc (1 mL), acetonitrile (1 mL) and water (1.5 mL) was added ruthenium chloride hydrate (2.8 mg, 0.012 mmol) and sodium meta-periodate (6.83 μl, 0.123 mmol) (portionwise over 5 minutes). The reaction was stirred at rt for 20 minutes and then partitioned between EtOAc (60 mL) and water (20 mL). The separated aqueous layer was extracted with EtOAc (2×20 mL) and the combined organic extracts were dried over MgSO4, filtered and evaporated in vacuo. Purification by column chromatography (12 g, SiO2, hexanes/IPA, 1:0 to 9:1) gave the title compound.

Workup

  1. custompartitioned between EtOAc (60 mL) and water (20 mL)
  2. extractionThe separated aqueous layer was extracted with EtOAc (2×20 mL)
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by column chromatography (12 g, SiO2, hexanes/IPA, 1:0 to 9:1)

Sources & evidence

ORD record
ord-0b438b978fd2453c935fe7b91bdef033
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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