HCID 69248394, compound → HCID 69247466, compound

HRID 475037Notes

Reaction equation

HRID 475037 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:10](=[O:11])[CH2:9][CH2:8][CH:7]([N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[N+:22]([O-])=O)[C:13]2=[O:25])[C:6]1=[O:26].[H][H]>[Pd].C1COCC1>[NH2:22][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[C:20](=[O:21])[N:12]([CH:7]1[CH2:8][CH2:9][C:10](=[O:11])[N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:6]1=[O:26])[C:13]2=[O:25]

Participants

5

Reactant 2

HCID 69248394HCID 69248394, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69247466HCID 69247466, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10% Pd/C (50 mg) was added to a THF solution of 2-(1-(2-methoxyethyl)-2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione (260 mg). The reaction vessel was pressurized with hydrogen gas at 5 times the atmospheric pressure. After 6 hrs of reaction time, the catalyst was filtered off and solvent was removed by rotary evaporation in vacuo yielding 218 mg of light-yellow solid. MS (m/e): 332 (M+H+).

Workup

  1. customAfter 6 hrs of reaction time
  2. filtrationthe catalyst was filtered off
  3. customsolvent was removed by rotary evaporation in vacuo

Sources & evidence

ORD record
ord-dfbd52a1cf904da9ab93505871c0521e
Source dataset
uspto-grants-2014_01
Patent number
US08637545B2

Reaction notes

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