Templates for exploratory library preparation. Derivatization of a functionalized spirocyclic 3,6-dihydro-2H-pyran formed by ring-closing metathesis reaction |
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Authors: | Walters Michael A La Frances Deshmukh Prashant Omecinsky Diana O |
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Institution: | Pfizer Global Research and Development, Ann Arbor Laboratories, 2800 Plymouth Road, Ann Arbor, Michigan 48105, USA. |
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Abstract: | The preparation of a novel spirocyclic template from tert-butoxycarbonyl-4-piperidone is reported. The synthesis of N-(tert-butoxycarbonyl)-1-oxa-9-aza-spiro5.5]undec-3-ene (4) for exploratory library generation involves ketone allylation, etherification, and ring-closing metathesis (RCM) reactions. Epoxidation of the alkene formed in the RCM followed by addition of volatile amines to the epoxides led rapidly to an exploratory library of structurally novel spirocyclic amino alcohols. The addition of amines to epoxides derived from 4 was determined to occur primarily at C3. |
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