Water → HCID 86755052, compound

HRID 1955407Notes

Reaction equation

HRID 1955407 reaction equation
[CH2:1]([N:8]1[CH2:16][C:15]2([C:17]([O:19][CH3:20])=[O:18])[CH:10]([C:11](I)=[CH:12][CH2:13][CH:14]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O.C(O[CH2:39][CH3:40])(=O)C>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:16][C:15]2([C:17]([O:19][CH3:20])=[O:18])[CH:10]([C:11]([C:40]3[CH:39]=[CH:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=3)=[CH:12][CH2:13][CH:14]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 86755053HCID 86755053, compound

Product 1

HCID 86755052HCID 86755052, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

240 mg of tetrakis(triphenylphosphine)palladium and then a solution of 0.69 g of 2-naphthylboronic acid, isolated in the trimer anhydride form, in 20 cm3 of methanol were added to a solution of 2 g of methyl (3aRS,4SR,7aRS)-2-benzyl-7-iodo4-phenyl-2,3,3a,4,5,7a-hexahydro-1H-isoindole-3a-carboxylate in 40 cm3 of toluene. 45 cm3 of a 2N aqueous sodium carbonate solution were added dropwise and the reaction mixture is brought to reflux for four hours. After cooling, 80 cm3 of water and 60 cm3 of ethyl acetate were added. The organic phase was separated by settling, washing with water to neutrality and dried over magnesium sulphate. After concentrating the solvent under reduced pressure, the residue was purified by flash chromatography on silica gel (230-400 mesh), elution being carried out with a mixture of cyclohexane and of ethyl acetate (90/10 by volume). 1.33 g (67%) of methyl (3aRS,4SR,7aRS)-2-benzyl-7-(2-naphthyl)-4-phenyl-2,3,3a,4,5,7a-hexahydro-1H-isoindole-3a-carboxylate were thus obtained in the form of a white foam, the characteristic of which was as follows:

Workup

  1. temperatureto reflux for four hours
  2. temperatureAfter cooling
  3. customThe organic phase was separated
  4. washwashing with water to neutrality
  5. dry with materialdried over magnesium sulphate
  6. concentrationAfter concentrating the solvent under reduced pressure
  7. customthe residue was purified by flash chromatography on silica gel (230-400 mesh), elution
  8. additionbeing carried out with a mixture of cyclohexane and of ethyl acetate (90/10 by volume)

Sources & evidence

ORD record
ord-ff5e7b3e689743f09227f22a2ef5d3cc
Source dataset
uspto-grants-2000_09
Patent number
US06124465

Reaction notes

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