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

HRID 1584585

反応式

HRID 1584585 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 86754370trans-hexahydro-N-acetylisoindoline収率 0.2%

試薬・触媒・溶媒 2

HCID 178503044HCID 178503044、化合物触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-47db33fc981c43b0bae87edf744595c0
出典データセット
uspto-grants-1999_08
特許番号
US05932744

関連ノート

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