Hydrochloric Acid → (3aR,4S,7aR)-7,7-diphenyl-2-[(2-pyrrolidinophenyl)acetyl]-4-perhydroisoindolol hydrochloride

Participants

Reaction Conditions

Reaction Steps

0.42 cm3 of triethylamine and 0.49 g of carbonyl-diimidazole are added to a solution, cooled to +4° C., of 0.86 g of the hydrobromide salt of (2-pyrrolidinophenyl)acetic acid in 20 cm3 of dry dichloromethane. The mixture is stirred for one hour at 4° C. and then a solution of 1 g of (3aR,4S,7aR)-7,7-diphenyl-4-perhydroisoindolol hydrochloride and 0.42 cm3 of triethylamine in 10 cm3 of dry dichloromethane, is added. The reaction mixture is stirred at room temperature for 24 hours, and then washed twice with 10 cm3 of water and then with an aqueous solution of sodium hydrogen carbonate, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The product, which is obtained in the form of a base, is converted to the hydrochloride by dissolving in the minimum amount of acetone, by treating with a solution of hydrochloric acid in ethyl ether, and by adding ethyl ether. The solid obtained is triturated in ethyl ether and then dried. 0.2 g of (3aR,4S,7aR)-7,7-diphenyl-2-[(2-pyrrolidinophenyl)acetyl]-4-perhydroisoindolol hydrochloride is obtained in the form of a beige solid.

Provenance & Evidence