- A CONCISE SYNTHESIS OF RACEMIC PYRIDOGLUTETHIMIDE AND ITS RESOLUTION USING CHIRAL STATIONARY PHASE HPLC
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We describe a 'one-pot' synthesis of the aromatase inhibitor pyridoglutethimide and its 3-octyl-analogue, together with details of the resolution of the former using chiral stationary phase hplc.
- Boss, Aileen M.,Clissold, Derek W.,Mann, John,Markson, Andrew J.,Thickitt, Christopher P.
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- Preparation of 2,6-dioxopiperidine derivatives
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3-Alkyl- or fluoroalkyl-3-(4-pyridyl)piperidine-2,6-diones, useful in the treatment of breast cancer, of formula STR1 wherein R represents an alkyl group having 2 to 10 carbon atoms or a fluoroalkyl group having 2 to 5 carbon atoms and A is hydrogen or an alkyl group having 1 to 4 carbon atoms, are prepared by reacting a 4-pyridylacetate with an alkyl or fluoroalkyl iodide, chloride or bromide, in the presence of a sterically bulky base and reacting the product with acrylamide in the presence of a sodium or potassium branched chain alkoxide. Preferably potassium t-butoxide is used in both stages and they are carried out sequentially at room temperature in an alcoholic or polar, aprotic solvent in a single reaction vessel.
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