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Title: The application of lipase mediated resolutions to the synthesis of the optical isomers of bufuralol and methadone
Author: Hull, Jonathan David
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2000
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This thesis describes the application of lipase mediated kinetic resolutions in the synthesis of two biologically active and pharmaceutically important compounds :- Bufuralol has activity as a beta-blocker and recently it has become useful in metabolism studies as a substrate for a specific cytochrome P450 enzyme. Chapter three details how bufuralol, formerly marketed as a racemate, can be conveniently prepared in optically enriched form with a lipase resolution of a precursor as the key step. Methadone is currently used worldwide as a treatment in the maintenance of patients with addictions to opiates. It is mainly administered as a racemic mixture although the activity of the drug is due to the levorotatory isomer only. Levo-methadone can be efficiently prepared by employing a lipase in the resolution of 1-dimethylamino-2-propanol which is an inexpensive starting material for the synthesis of methadone. This is described in chapter four. Since both isomers of 1-dimethylamino-2-propanol are isolated from the resolution dextro-methadone may also be prepared and although it shows little or no activity itself, dextro-methadone may be converted in two steps to levo-α-acetylmethadol which is used in the U.S. as a longer acting alternative to methadone.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available