Synthesis of some hydroxymethyl- and aminomethyl-indolizines

Abstract

Syntheses are reported of 2-hydroxymethylindolizine (4), 3-hydroxymethylindolizine (5), and 2-methyl-6-hydroxymethylindolizine (6). Attempts to prepare 1-hydroxymethyl-2-methylindolizine by reduction of the corresponding ethoxycarbonyl derivative or by a Chichibabin synthesis from a 2-pyridylethanol derivative were unsuccessful, although 1-(2-hydroxyethyl)-2-methylindolizine (13) was so obtained. The very unstable 2-aminomethyl-indolizine (15) and 7-aminomethyl-2-methylindolizine (34) have been obtained by reduction of the corresponding nitriles; attempts to obtain 6-aminomethyl-2-methylindolizine are described.