diethyl(S)-2-(4-nitrophthalimido)glutarate → diethyl(S)-2-(4-aminophthalimido)glutarate

HRID 1369451Notes

Reaction equation

HRID 1369451 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([C@@H:13]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8](=[O:9])[C:7]2=[CH:26][CH:27]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([C@@H:13]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8](=[O:9])[C:7]2=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 10429715diethyl(S)-2-(4-nitrophthalimido)glutarate

Product 1

HCID 10043327diethyl(S)-2-(4-aminophthalimido)glutarateYield 88.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of diethyl (S)-2-(4-nitrophthalimido)glutarate (35.6 g, 94.1 mmol) and 10% palladium on carbon (0.5 g) (Aldrich) in ethanol (200 ml) was shaken under a hydrogen atmosphere (40-50 psi) for 26 hours. The solution was filtered through celite and concentrated in vacuo. The residue was purified by chromatography on silica gel (250 g) eluting with diethyl ether:hexane (4:1) to give diethyl (S)-2-(4-aminophthalimido)glutarate as a viscous yellow oil (29.1 g).

Workup

  1. filtrationThe solution was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel (250 g)
  4. washeluting with diethyl ether:hexane (4:1)

Sources & evidence

ORD record
ord-444e09ad0c914aee9f811de418b3d4f1
Source dataset
uspto-grants-2003_06
Patent number
US06579877B2

Reaction notes

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