Collect. Czech. Chem. Commun. 1983, 48, 1759-1764

The synthesis of some alcohols derived from 1,2,3,4-tetrahydroisoquinoline and from 1,2,3,4-tetrahydroquinoline

Miloslav Ferles, Alexandra Šilhánková, Stanislav Kafka, Petr Taufmann and Tomáš Motáček

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


Reduction of ethyl esters of ω-(1,2,3,4-tetrahydro-2-isoquinolyl)alkanoic acids IVa-e by means of LiAlH4 was used for the preparation of corresponding primary alcohols Ia-e. 6-(1,2,3,4-Tetrahydro-2-isoquinolyl)-1-hexanol (Ie) was also obtained on reduction of ester amide VII. Reduction of 2-(2-hydroxypropanoyl)-1,2,3,4-tetrahydroisoquinoline (V) with LiAlH4 gave secondary alcohol II; in the quinoline series alcohol IIIa was obtained in a similar manner by reduction of ethyl 3-(1,2,3,4-tetrahydro-1-quinolyl)propanoate (IIIb).