Synthesis of indolizidine from N-chlorooctahydro-1-pyrindine

Author

Jacalyn Mary Schremmer

Date of Award

6-1981

Degree Type

Thesis

Degree Name

Master of Science

Major

Chemistry

Major Professor

Fred M. Schell

Committee Members

Paul R. Williams

Abstract

A model study was undertaken to investigate the rearrangement of N-chloro-octahydro-1-pyrindine. Cyclopenteno-2,3-pyridine was reduced catalytically to a mixture of the cis- and trans-isomers of octahydro-1-pyrindine. The N-chloramines were prepared, and rearrangement was accomplished by stirring these with silver tetrafluoroborate in benzene under a nitrogen atmosphere. The indolizidinium ion which resulted was isolated and reduced with sodium cyanoborohydride. Indolizidine was obtained in 85% yield, based on recovered octahydro-1-pyrindine. Attempts are described to capture the indolizidinium ion with various nucleophiles.

Recommended Citation

Schremmer, Jacalyn Mary, "Synthesis of indolizidine from N-chlorooctahydro-1-pyrindine. " Master's Thesis, University of Tennessee, 1981.
https://trace.tennessee.edu/utk_gradthes/15288