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

HRID 1584585

반응식

HRID 1584585 반응식
[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]

참가 물질

6

반응물 3

HCID 154443561-(2,3-dihydro-1H-isoindol-2-yl)ethan-1-oneHCID 54454143cis-hexahydro-N-acetylisoindolineHCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 86754370trans-hexahydro-N-acetylisoindoline수율 0.2%

시약·촉매·용매 2

HCID 178503044HCID 178503044, 화합물촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-47db33fc981c43b0bae87edf744595c0
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05932744

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