HCID 54553080, compound → Mitiglinide

HRID 1590180Notes

Reaction equation

HRID 1590180 reaction equation
[CH2:1]([C@@H:8]([CH2:19][C:20]([N:22]1[CH2:30][C@H:29]2[C@H:24]([CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:23]1)=[O:21])[C:9]([O:11]CC1C=CC=CC=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[CH2:1]([C@@H:8]([CH2:19][C:20]([N:22]1[CH2:23][C@H:24]2[C@H:29]([CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:30]1)=[O:21])[C:9]([OH:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 54553080HCID 54553080, compound

Product 1

HCID 121891MitiglinideYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl (S)-2-benzyl-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionate (400 mg) in ethyl acetate (3 ml) was added 10% Pd-C (60 mg) and the mixture was hydrogenolyzed at room temperature and atmospheric pressure for 16 hours. After the catalyst was filtered off, the solvent was evaporated under reduced pressure to give 227 mg of (S)-2-benzyl-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acid as a colorless viscous oil.

Workup

  1. customwas hydrogenolyzed at room temperature
  2. filtrationAfter the catalyst was filtered off
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-94c6f5ca94314f32bd5a818ee95cd2b0
Source dataset
uspto-grants-1993_04
Patent number
US05202335

Reaction notes

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