1-(2,3-dihydro-1H-isoindol-2-yl)ethan-1-one → trans-hexahydro-N-acetylisoindoline

HRID 1584585

Reaction equation

HRID 1584585 reaction equation
[C:1]([N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].[H][H].C(N1C[C@H]2[C@H](CCCC2)C1)(=O)C>[C].[Ru].CO>[C:1]([N:4]1[CH2:12][C@H:11]2[C@@H:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 154443561-(2,3-dihydro-1H-isoindol-2-yl)ethan-1-oneHCID 54454143cis-hexahydro-N-acetylisoindolineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 86754370trans-hexahydro-N-acetylisoindolineYield 0.2%

Reagents, catalysts & solvents 2

HCID 178503044HCID 178503044, compoundCatalystHCID 887MethanolSolvent

Procedure

In a 3-liter GL autoclave fitted with a electromagnetic stirrer are added 175 g of N-acetylisoindoline, 825 g of methylalcohol and 17 g of 5% ruthenium-carbon catalyst (50% water-containing). The reaction mixture is subjected to a hydrogen-pressure of 20 kg/cm2 and a temperature of 110° C. After a 8 hour hydrogen introduction, the drop in the rate of the hydrogen-absorption is observed, at this point the introduction of hydrogen is ceased to terminate the reaction. After the termination of reaction, the catalyst is filtered out from the reacted solution. By the result of the capillary chromatographic analysis, the yield of cis-hexahydro-N-acetylisoindoline is 93.7%. In addition, 0.2% of trans-hexahydro-N-acetylisoindoline is formed.

Workup

  1. customIn a 3-liter GL autoclave fitted with a electromagnetic stirrer
  2. customa temperature of 110° C
  3. customthe drop in the rate of the hydrogen-absorption
  4. customto terminate
  5. customthe reaction
  6. customAfter the termination of reaction
  7. filtrationthe catalyst is filtered out from the reacted solution
  8. customBy the result of the capillary chromatographic analysis

Sources & evidence

ORD record
ord-47db33fc981c43b0bae87edf744595c0
Source dataset
uspto-grants-1999_08
Patent number
US05932744

Linked notes

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