(3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol → (3aRS,4RS,5RS,7aSR)-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.5 g of (3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol and 120 cm3 of anhydrous ethanol is heated to 60° C. with stirring; 0.49 g of 20% palladium hydroxide on charcoal is added and the reaction mixture is then hydrogenated, with stirring, at a temperature of 60° C. and at atmospheric pressure. After reaction for 2 hours, 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 crystallized in 50 cm3 of isopropyl ether. 1.02 g of (3aRS,4RS,5RS,7aSR)-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol are obtained, melting at 168° C.

Provenance & Evidence