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)perhydro-4,5-isoindolediol and 50 cm3 of ethanol is heated to 65° C. with stirring; 0.65 g of 20% palladium hydroxide on charcoal is added, and the reaction mixture is then hydrogenated, with stirring, at a temperature of 65° C. and at atmospheric pressure. After reaction for 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 crystallized in 10. cm3 of isopropyl ether. 1.45 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol are obtained, melting at 230° C.

Provenance & Evidence