HCID 18651164, compound → HCID 54078901, compound

HRID 1590185Notes

Reaction equation

HRID 1590185 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[S:22][CH:21]=[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[S:22][CH:21]=[CH:20][CH:19]=1)[C:14]([OH:16])=[O:15])=[O:11]

Participants

4

Reactant 1

HCID 18651164HCID 18651164, compound

Product 1

HCID 54078901HCID 54078901, compoundYield 19.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of (E)-3-(cis-hexahydro-2-isoindolinylcarbonyl)-2-(2-thenylidene)propionic acid (150 mg) in ethanol (20 ml) was added 10% Pd-C (70 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. The residue was purified by thin layer chromatography (mobile phase: dichloromethane/methanol=15/1) to give 30 mg of 3-(cis-hexahydro-2-isoindolinylcarbonyl)-2-(2-thenyl)propionic acid as a pale yellow viscous oil.

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 purified by thin layer chromatography (mobile phase: dichloromethane/methanol=15/1)

Sources & evidence

ORD record
ord-40738ee7cba84d9b9d82edbc469bcaff
Source dataset
uspto-grants-1993_04
Patent number
US05202335

Reaction notes

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