Collect. Czech. Chem. Commun. 1984, 49, 78-85

Hydroboration of 1-(3-butenyl)piperidine and 1-(4-pentenyl)piperidine

Stanislav Kafka and Miloslav Ferles

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


Hydroboration of 1-(3-butenyl)- (Ia and 1-(4-pentenyl)piperidine (Ib) with triethylamineborane followed by hydrolysis and oxidation afforded the appropriate alcohols IIIc and IIIf resp. The spirocyclic amine-borane IIa,b isolated from the hydroboration products were transformed by hydrochloric acid into the hydrochlorides of piperidinealkylboronic acids IVa,b which were oxidized in an alkaline medium with hydrogen peroxide to the primary alcohols IIIc,f. Diethyl ester V was prepared by ethanolysis of IIa.