THE INVESTIGATION FOR ALTERNATE METHODS FOR THE SYNTHESIS OF 3-QUINUCLIDINOL AND OTHER AZABICYCLIC ALCOHOLS.

Abstract

An attempt was made to synthesize 3-Quinuclidinol from 4-ethylpyridine using a multiple step sequence in which the last step was the photochemical rearrangement and ring closure of an N-chloro-4-ethylpiperidine derivative. No 3-Quinuclidinol was detected in the products when the alpha-acetoxy- or alpha-hydroxyethylpiperidine derivatives were used. It was postulated that this failure may be due to carbonium ion formation in the acid solvent utilized in the photochemical step. A derivative more resistant to carbonium ion formation, 4 (alpha-methoxyethyl) piperidine, was synthesized, but lack of time prevented its use in the photochemical step. (Author)

Document Details

Document Type
Technical Report
Publication Date
May 15, 1964
Accession Number
AD0612360

Entities

People

  • Jimmie S. Payne Jr.

Organizations

  • Tracor

Tags

DTIC Thesaurus Topics

  • 1-Ring Heterocyclic Compounds
  • Chemical Compounds
  • Cyclic Compounds
  • Heterocyclic Compounds
  • Sequences

Fields of Study

  • Chemistry

Readers

  • Applied Combinatorial Optimization and Logic Circuit Design.
  • Organic Chemistry