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Synthesis of 2,3-dihydrospiro[benzofuran-2,4′ -piperidines] and 2,3-dihydrospiro[benzofuran-2,3′-pyrrolidines]
Authors:Richard C Effland  Beth Ann Gardner  Joseph Strupczewski
Abstract:The synthesis of 2,3-dihydrospirobenzofuran-2,4′-piperidines] 3 and 2,3-dihydrospirobenzofuran-2,3′]-pyrrolidine] 6 is described. The synthesis was achieved by a Grignard reaction of a 2-fluorobenzylhalide with an appropriate cycloazaalkyl ketone to yield the tertiary alcohols 1 and 4 . Subsequent intramolecular displacement of the aromatic fluoride by the derived alkoxides provided the novel system. Nitration of 1′-acetyl-2,3-dihydrospirobenzofuran-2,4′-piperidine] 7 resulted in a 5-nitro derivative.
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