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Paper | Regular issue | Vol 34, No. 1, 1992, pp.135-148
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5906
Synthesis and Rearrangement of Aminoalkyl Lactones to Spirocyclic Hydroxymethyl Lactams

Claudia Dostal, Silvia Lauritz, and Ernst Urban*

*Institut für Pharmazeutische Chemie, Universität Wien, Währinger Strasse, A-1090 Wien, Austria


Lithiation of lactones (1) and (2) followed by electrophilic substitution with dibromoalkanes afforded bromoalkyl lactones (3a -3c) and (4a - 4c). Treatment of 3a, 3b, 4a, and 4b with primary amines led to formation of aminoalkyl lactones (5a, 5b, 6a, 6b amd 11), which were rearranged to spirocyclic hydroxyalkyl lactams (7a, 7b, 8a, 8b and 12). Spirocyclic lactams (7a, 7b, 8a and 8b) were reduced to spirocyclic amines (9a, 9b, 10a and 10b), whereas reduction of lactam (12) gave a separable mixture of amine (13) and tricyclic aminal (15).