Collect. Czech. Chem. Commun. 1983, 48, 1068-1073

On hydroboration of 2-allyl-1,2,3,4-tetrahydroisoquinoline

Miloslav Ferles and Stanislav Kafka

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6


Heating of 2-allyl-1,2,3,4-tetrahydroisoquinoline (I) with triethylamine-borane afforded 7,8-benzo-5-aza-1-boraspiro[4,5]decane (II) which was hydrolyzed with hydrochloric acid to 3-(1,2,3,4-tetrahydro-2-isoquinolyl)propylboronic acid hydrochloride (III). Ethanolysis of II led to the diethyl ester IV. Compounds II and III were oxidizes to give 3-(1,2,3,4-tetrahydro-2-isoquinolyl)-1-propanol (V).