HCID 12221967, compound → HCID 86754369, compound

HRID 1584584Notes

Reaction equation

HRID 1584584 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].[H][H].C(OC(N1C[C@H]2[C@H](CCCC2)C1)=O)C>[C].[Rh].C(O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][C@H:8]2[C@@H:13]([CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:14]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 12221967HCID 12221967, compoundHCID 13097838Ethyl 1,3-dihydro-2H-isoindole-2-carboxylateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 86754369HCID 86754369, compoundYield 0.6%

Reagents, catalysts & solvents 2

HCID 178503043HCID 178503043, compoundCatalystHCID 702EthanolSolvent

Procedure

In a 3-liter GL autoclave fitted with a electromagnetic stirrer are added 207 g of N-ethoxycarbonylisoindoline, 793 g of ethylalcohol and 20 g of 5% rhodium-carbon catalyst (50% water-containing). The reaction mixture is subjected to a hydrogen-pressure of 25 kg/cm2 and a temperature of 130° C. After a 10 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-ethoxycarbonylisoindoline is 95.3%. In addition, 0.6% of trans-hexahydro-N-ethoxycarbonylisoindoline is formed.

Workup

  1. customIn a 3-liter GL autoclave fitted with a electromagnetic stirrer
  2. customa temperature of 130° 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-034b8c9a734c4d5795201b41b3a1a7ad
Source dataset
uspto-grants-1999_08
Patent number
US05932744

Reaction notes

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