HCID 21783200, compound → HCID 70071916, compound

HRID 1654656Notes

Reaction equation

HRID 1654656 reaction equation
[CH2:1]([N:9]1[C:13](=[O:14])[C@H:12]2[CH2:15][CH:16]=[CH:17][CH2:18][C@H:11]2[C:10]1=[O:19])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].CC1C=CC(C)=CC=1>[CH2:1]([N:9]1[C:13](=[O:14])[C@H:12]2[CH2:15][CH2:16][CH:17]=[CH:18][C@H:11]2[C:10]1=[O:19])[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 21783200HCID 21783200, compound

Product 1

HCID 70071916HCID 70071916, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 7809P-XyleneSolvent

Procedure

A mixture of 5.0 g of cis-N-phenethyl-1,2,3,6-tetrahydrophthalimide (prepared by the method of Example 1), 0.5 g of chlorotris(triphenylphosphine)rhodium and 50 mL of p-xylene was heated under reflux for 48 hours. Removal of the solvent and short-path distillation of the residue (150° bath temperature, 0.001 mm) gave 4.72 g of cis-N-phenethyl-1,2,3,4-tetrahydrophthalimide containing 12% of unrearranged starting material.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. customRemoval of the solvent and short-path distillation of the residue (150° bath temperature, 0.001 mm)

Sources & evidence

ORD record
ord-39dc0a149b5e43acb9324cfdc7536e7b
Source dataset
uspto-grants-1995_04
Patent number
US05409929

Reaction notes

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