Hydrochloric Acid → HCID 67916057, compound

Participants

Reaction Steps

(3aRS,7aRS)-2-[(2-(tert-butoxycarbonylaminomethyl)phenyl)acetyl]-7,7-diphenyl-4-perhydroisoindolone (1 g) is treated with a 5.7N solution (10 cc) of hydrochloric acid in dry dioxane at 20° C. for 16 hours. The reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) and the residue is solidified by scratching with isopropyl ether and reprecipitated by cooling a solution in boiling acetonitrile (20 cc). The solid is drained, washed with isopropyl ether and dried. The solid is dissolved in water, the solution is filtered, rendered alkaline to pH 10 by the action of a decinormal sodium hydroxide solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulphate and filtered and the filtrate is treated with a 3N solution (1 cc) of hydrochloric acid in dioxane. The precipitate is drained, washed with isopropyl ether and dried. (3aRS,7aRS)-2-[(2-aminomethylphenyl)acetyl]-7,7-diphenyl-4-perhydroisoindolone (0.5 g) is obtained in the form of a cream-white solid.

Provenance & Evidence