14-hydroxycodeine and derivatives

Currie, Andrew Cochran (1961) 14-hydroxycodeine and derivatives. PhD thesis, University of Glasgow.

Abstract

A series of 14-substituted codeine derivatives were prepared for pharmacological study by sodium borohydride reduction of the corresponding 14-hydroxy and 14-acyloxycodeinones. The epimeric 14-substituted isocodeines were not formed by this reaction but were prepared using 14-hydroxycodeine tosylate as an intermediate. The latter compound on treatment with 70% acetic acid gave the l4-hydroxyallopseudocodeine series. Lithium aluminium hydride reduction of 14-hydroxycodeine tosylate gave 14-hydroxydeoxycodeine and the very active analgesics, the 14-acyloxydeoxycodeines. Attempts to prepare known codeine derivatives from "hydroxy-codeine", the non-phenolic compound from the reaction of zinc dust and acetic acid on 14-hydroxycodeinone are described and a new structure is postulated. A new method is reported for the synthesis of 14-hydroxy-N-alkylnorcodeines. This involves the formation of 14-hydroxy-N-acylnorcodeine derivatives from the corresponding 14-acyloxy-N-cyano compound by acyl migration, and their reduction with lithium aluminium hydride.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Additional Information: Adviser: P L Pauson
• Keywords: Pharmacology
• Date of Award: 1961
• Depositing User: Enlighten Team
• Unique ID: glathesis:1961-72537
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 11 Jun 2019 11:06
• Last Modified: 11 Jun 2019 11:06
• URI: https://theses.gla.ac.uk/id/eprint/72537