HCID 67999562, compound → HCID 58573416, compound

HRID 932097Notes

Reaction equation

HRID 932097 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([C@@H:21]([CH2:26][CH3:27])[CH:22]=[CH:23][C:24]#[N:25])[C:11](=[O:28])[C@:10]([CH2:30][CH:31]3[CH2:35][O:34][C:33]([CH3:37])([CH3:36])[O:32]3)([CH3:29])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[H][H]>CCO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)[N:12]([C@@H:21]([CH2:26][CH3:27])[CH2:22][CH2:23][C:24]#[N:25])[C:11](=[O:28])[C@:10]([CH2:30][CH:31]3[CH2:35][O:34][C:33]([CH3:36])([CH3:37])[O:32]3)([CH3:29])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67999562HCID 67999562, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58573416HCID 58573416, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (4S)-4-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3-methyl-2-oxopiperidin-1-yl)hex-2-enenitrile prepared above in Step E (208 mg, 0.384 mmol) in EtOH (12.8 mL) was added 10% palladium on activated carbon (40.9 mg, 0.038 mmol). Then the reaction mixture was subjected to regular hydrogenation with hydrogen (0.774 mg, 0.384 mmol). After being stirred at rt for 1.5 h, the catalyst was filtered using a short plug of silica-gel and washed (EtOAc). The combined organic solutions were concentrated under reduced pressure. Purification by combi flash (flash column chromatography, Teledyne Isco, Lincoln, Nebr.) (SiO2, 24 g, 35% and 40% EtOAc/Hexanes) provided the title compound as a colorless film.

Workup

  1. filtrationthe catalyst was filtered
  2. washwashed (EtOAc)
  3. concentrationThe combined organic solutions were concentrated under reduced pressure
  4. customPurification by combi flash (flash column chromatography, Teledyne Isco, Lincoln, Nebr.) (SiO2, 24 g, 35% and 40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-82cafcbd7fa048a6bf589bfad7d912aa
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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