Sodium Carbonate → HCID 86755056, compound

Participants

Reaction Steps

By carrying out the reaction as in Stage C of Example 45, but from 1.2 g of methyl (3aRS,4SR,7aRS)-2-benzyl-7-iodo-4-phenyl-2,3,3a,4,5,7a-hexahydro-1H-isoindole-3a-carboxylate in 30 cm3 of toluene, from 150 mg of tetrakis(triphenylphosphine)palladium, from 0.35 g of 3-thienylboronic acid in 15 cm3 of methanol and from 28 cm3 of a 2N aqueous sodium carbonate solution at reflux for three hours, 0.99 g (93%) of methyl (3aRS,4SR,7aRS)-2-benzyl-4-phenyl-7-(3-thienyl)-2,3,3a,4,5,7a-hexahydro-1H-isoindole-3a-carboxylate was obtained, after purification by flash chromatography on silica gel (230-400 mesh), elution being carried out with a mixture of cyclohexane and ethyl acetate (85/15 by volume), in the form of a yellow oil, the characteristic of which was as follows:

Provenance & Evidence