HCID 67758059, compound → HCID 53849277, compound

HRID 1590184Notes

Reaction equation

HRID 1590184 reaction equation
[CH2:1]1[C@@H:9]2[C@@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][N:2]1[C:10]([CH2:12]/[C:13](=[CH:17]\[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)/[C:14]([OH:16])=[O:15])=[O:11]>C(O)C.[Pd]>[CH2:1]1[C@@H:9]2[C@@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][N:2]1[C:10]([CH2:12][CH:13]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=1)[C:14]([OH:16])=[O:15])=[O:11]

Participants

4

Reactant 1

HCID 67758059HCID 67758059, compound

Product 1

HCID 53849277HCID 53849277, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of (E)-3-(cis-hexahydro-2-isoindolinylcarbonyl)-2-(4-methylbenzylidene)propionic acid (250 mg) in ethanol (10 ml) was added 10% Pd-C (20 mg) and the mixture was hydrogenated at room temperature and atmospheric pressure for 16 hours. After the catalyst was filtered off, the solvent was evaporated under reduced pressure and the residue was crystallized from diethyl ether to give 220 mg of 3-(cis-hexahydro-2-isoindolinylcarbonyl)-2-(4-methylbenzyl)propionic acid.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationAfter the catalyst was filtered off
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-5315640056ba4d509982b4feea6cf79a
Source dataset
uspto-grants-1993_04
Patent number
US05202335

Reaction notes

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