(+/-)-Benzyl 3-(1,3-dioxoisoindolin-2-yl)-4-fluoropiperidine-1-carboxylate → cis-(+/-)-2-(4-Fluoropiperidin-3-yl)isoindoline-1,3-dione

HRID 69896Notes

Reaction equation

HRID 69896 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[CH:17]([F:18])[CH2:16][CH2:15][N:14](C(OCC2C=CC=CC=2)=O)[CH2:13]1>C(O)C.C(OCC)(=O)C.[Pd]>[F:18][C@H:17]1[CH2:16][CH2:15][NH:14][CH2:13][C@H:12]1[N:3]1[C:2](=[O:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=[O:11]

Participants

5

Reactant 1

HCID 86669189(+/-)-Benzyl 3-(1,3-dioxoisoindolin-2-yl)-4-fluoropiperidine-1-carboxylate

Product 1

HCID 68184614cis-(+/-)-2-(4-Fluoropiperidin-3-yl)isoindoline-1,3-dione

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (+/−)-benzyl 3-(1,3-dioxoisoindolin-2-yl)-4-fluoropiperidine-1-carboxylate (1.0 equiv.) in ethanol and ethyl acetate (1:1, 0.2 M solution) was added Pd/C (20 wt %) under N2 atmosphere. The reaction mixture was flushed with H2 gas, equipped with H2 gas balloon, and stirred for 16 h at room temperature. The reaction mixture was filtered through Celite® Pad and the filtrate was dried in vacuo. The crude (+/−)-2-(4-fluoropiperidin-3-yl)isoindoline-1,3-dione was used for the next step without further purification (>99%). LCMS (m/z): 249.1 (MH+), Rt=0.49 min.

Workup

  1. customThe reaction mixture was flushed with H2 gas
  2. customequipped with H2 gas balloon
  3. filtrationThe reaction mixture was filtered through Celite® Pad
  4. customthe filtrate was dried in vacuo
  5. customThe crude (+/−)-2-(4-fluoropiperidin-3-yl)isoindoline-1,3-dione was used for the next step without further purification (>99%)

Sources & evidence

ORD record
ord-4c57a690129d4c00a665c3fd8a179fa3
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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