2-((4,4-Difluoro-1-((S)-1-phenylethyl)piperidin-2-yl)methyl)isoindoline-1,3-dione → 2-((4,4-Difluoropiperidin-2-yl)methyl)isoindoline-1,3-dione

HRID 61148Notes

Reaction equation

HRID 61148 reaction equation
[F:1][C:2]1([F:28])[CH2:7][CH2:6][N:5]([C@H](C2C=CC=CC=2)C)[CH:4]([CH2:16][N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:27])[CH2:3]1>C(O)(=O)C.[Pd]>[F:28][C:2]1([F:1])[CH2:7][CH2:6][NH:5][CH:4]([CH2:16][N:17]2[C:18](=[O:27])[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:25]2=[O:26])[CH2:3]1

Participants

4

Reactant 1

HCID 1177281942-((4,4-Difluoro-1-((S)-1-phenylethyl)piperidin-2-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 1177280172-((4,4-Difluoropiperidin-2-yl)methyl)isoindoline-1,3-dioneYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-((4,4-difluoro-1-((S)-1-phenylethyl)piperidin-2-yl)methyl)isoindoline-1,3-dione (1.1 g, 2.86 mmol) in acetic acid (10 mL) was added 10% Pd/C (200 mg). The reaction was then stirred under H2 until HPLC indicated complete removal of the phenethyl group. The reaction was the filtered through diatomaceous earth and concentrated. The crude residue was then dissolved in EtOAc and washed with saturated NaHCO3, brine, dried (MgSO4), and concentrated to yield the title compound as an orange oil (720 mg, 90%).

Workup

  1. customremoval of the phenethyl group
  2. filtrationfiltered through diatomaceous earth
  3. concentrationconcentrated
  4. dissolutionThe crude residue was then dissolved in EtOAc
  5. washwashed with saturated NaHCO3, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f40189809fc0463280f36e55f515a021
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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