p-Toluenesulfonic acid → 4-Amino-2-(3-fluoro-5-hydroxy-2,6-dioxopiperid-3-yl)isoindoline-1,3-dione

HRID 892001Notes

Reaction equation

HRID 892001 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:25])[N:5]([C:12]1([F:24])[CH2:17][CH:16]([O:18]C(=O)C)[C:15](=[O:22])[NH:14][C:13]1=[O:23])[C:6]2=[O:11].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:25])[N:5]([C:12]1([F:24])[CH2:17][CH:16]([OH:18])[C:15](=[O:22])[NH:14][C:13]1=[O:23])[C:6]2=[O:11]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 222412033-(4-Amino-1,3-dioxoisoindolin-2-yl)-3-fluoro-2,6-dioxo-5-acetoxypiperidine

Product 1

HCID 222412064-Amino-2-(3-fluoro-5-hydroxy-2,6-dioxopiperid-3-yl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(4-amino-1,3-dioxoisoindolin-2-yl)-3-fluoro-2,6-dioxo-5-acetoxypiperidine (1 g, 2.9 mmol) and p-toluenesulfonic acid. (0.28 g, 1.5 mmol) in methanol (10 mL) is heated at reflux for 5 h. The solvent is removed in vacuo to give 4-amino-2-(3-fluoro-5-hydroxy-2,6-dioxopiperid-3-yl)isoindoline-1,3-dione which is further purified by column chromatography.

Workup

  1. temperatureat reflux for 5 h
  2. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-8bbcc4c448064fbb85e1d6caa4543039
Source dataset
uspto-grants-2006_02
Patent number
US07005438B2

Reaction notes

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