cis-1,2,3,6-Tetrahydrophthalimide → 1H-Isoindole-1,3(2H)-dione, hexahydro-

HRID 1025539

Reaction equation

HRID 1025539 reaction equation
[C:1]1(=[O:11])[C@@H:9]2[C@@H:4]([CH2:5][CH:6]=[CH:7][CH2:8]2)[C:3](=[O:10])[NH:2]1>CO.[Pd]>[C:1]1(=[O:11])[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[C:3](=[O:10])[NH:2]1

Participants

4

Reactant 1

HCID 92888cis-1,2,3,6-Tetrahydrophthalimide

Product 1

HCID 735591H-Isoindole-1,3(2H)-dione, hexahydro-Yield 85.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (3aR,7aS)-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione (3.0 g, 19.9 mmol) and 10% Pd/C (300 mg) in MeOH (100 mL) was shaken in an H2 atmosphere (300 psi) in a Parr apparatus for 24 h. The reaction mixture was filtrated and the liquids concentrated to dryness, affording the title compound (2.6 g, 16.99 mmol), that was sued without any further purification, as a white powder.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. concentrationthe liquids concentrated to dryness

Sources & evidence

ORD record
ord-eebc4f521baf4b0f85da8ce609a1ac54
Source dataset
uspto-grants-2014_05
Patent number
US08729098B2

Linked notes

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