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

HRID 1584585

Reaktionsgleichung

Reaktionsgleichung von HRID 1584585
[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]

Komponenten

6

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-47db33fc981c43b0bae87edf744595c0
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05932744

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