2-Benzyl-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol → (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol

Participants

Reaction Conditions

Reaction Steps

A mixture of 2 g of (3aRS,4RS,5RS,7aRS)-2-benzyl-7,7-diphenyl-4-(2-methoxyphenyl)-perhydroisoindole-4,5-diol and 50 cm3 of ethanol is heated at 65° C., while stirring; 0.65 g of 20% palladium hydroxide-on-charcoal is added and the reaction mixture is then hydrogenated at a temperature of 65° C. and under atmospheric pressure, while stirring. After a reaction time of 1 hour, the theoretical volume of hydrogen has been absorbed; the reaction mixture is filtered and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallised in 10 cm3 of isopropyl ether. 1.45 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-perhydroisoindole-4,5-diol which melts at 230° C. are obtained.

Provenance & Evidence