Collect. Czech. Chem. Commun. 1983, 48, 1435-1439

Syntheses of some ω-(1,2,3,6-tetrahydro-1-pyridyl)-1-alkanols

Alexandra Šilhánková, Jiří Lávička, Stanislav Kafka and Miloslav Ferles

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


Quaternary salts of pyridine and 4-methylpyridine with ethyl esters of ω-bromoalkanoic acids, IIa-IIe, were converted into esters IIIa-IIIe by the action of sodium borohydride. These were further reduced by lithium aluminium hydride to alcohols Ia-Ie. 4-(1,2,3,6-Tetrahydro-1-pyridyl)-butanol (Ic) was also obtained from 1-(3-ethoxycarbonylpropyl)pyridinium bromide(IIc) by the action of LiAlH4. The ethyl ester IIIa was converted into amide IV.