2-Methoxyphenylacetic acid → (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-(2-methoxyphenyl)-acetylperhydroisoindole-4,5-diol

Participants

Reaction Steps

To a solution of 4.5 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol hydrochloride in 100 cm3 of dichloromethane, cooled to 0° C., are added 4.2 cm3 of triethylamine, followed by 2.4 g of (2-methoxyphenyl)acetic acid in 50 cm3 of dichloromethane. Stirring is carried out at room temperature for 90 minutes; the reaction mixture is washed with twice 10 cm3 of water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The crystallized solid is taken up with 100 cm3 of diisopropyl ether and then filtered, washed with 50 cm3 of saturated sodium bicarbonate solution and then with 50 cm3 of diisopropyl ether. 4.35 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-(2-methoxyphenyl)acetylperhydro-4,5-isoindolediol are obtained, in the form of a light beige solid melting at 278° C.

Provenance & Evidence