4-Methyl-1,3-isobenzofurandione → 3-(4-Methyl-1,3-dioxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine

HRID 891983Notes

Reaction equation

HRID 891983 reaction equation
[O:1]=[C:2]1[CH:7]([NH:8][C:9]([O:11]CC2C=CC=CC=2)=O)[CH2:6][CH:5]([O:19][C:20](=[O:22])[CH3:21])[C:4](=[O:23])[NH:3]1.C[C:25]1[CH:35]=[CH:34][CH:33]=[C:27]2[C:28](O[C:31](=O)[C:26]=12)=[O:29]>C(O)(=O)C.[Pd]>[CH3:31][C:26]1[CH:25]=[CH:35][CH:34]=[C:33]2[C:27]=1[C:28](=[O:29])[N:8]([CH:7]1[CH2:6][CH:5]([O:19][C:20](=[O:22])[CH3:21])[C:4](=[O:23])[NH:3][C:2]1=[O:1])[C:9]2=[O:11]

Participants

5

Reactant 2

HCID 985004-Methyl-1,3-isobenzofurandioneHCID 12047333HCID 12047333, compound

Product 1

HCID 120473343-(4-Methyl-1,3-dioxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2,6-dioxo-3-benzyloxycarbonylamino-5-acetoxypiperidine (9 g, 28.2 mmol) (U. Teubert et al, Arch. Pharm. Pharm. Med. Chem. (1998) 7–12) and Pd/C (10%, 0.9 g) in acetic acid (90 mL) is shaken under hydrogen (50–60 psi) for 3 hours. The suspension is filtered through a pad of Celite and washed with acetic acid. To the filtrate is added 3-methylphthalic anhydride (4.56 g, 28.2 mmol) and this mixture is heated at reflux for 18 hours. The solvent is removed in vacuo to give 3-(4-methyl-1,3-dioxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine which can be further purified by column chromatography.

Workup

  1. filtrationThe suspension is filtered through a pad of Celite
  2. washwashed with acetic acid
  3. temperaturethis mixture is heated
  4. temperatureat reflux for 18 hours
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-794f7db6c22b4df3adef3dbfcfb6b9be
Source dataset
uspto-grants-2006_02
Patent number
US07005438B2

Reaction notes

Loading…