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Communication | Regular issue | Vol 31, No. 1, 1990, pp.23-26
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5228
Synthesis of 1,2,3,4,5,6-Hexahydro-8-hydroxy-2,6-epithio-3-benzazocine

Mikio Hori,* Hiroyuki Ozeki, Tatsunori Iwamura, Hiroshi Shimizu, Tadashi Kataoka, and Noriyuki Iwata

*Department of Pharmacognosy, Gifu College of Pharmacy, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan


In anticipation of diminishing narcotism of 1,2,3,4,5,6-hexahydro-8-hydroxy-2,6-methano-3-benzazocine opioids, the corresponding 2,6-epithio-3-benzazocines (2) have been synthesized by intramolecular cyclization of 1-(2-aminoethyl)-3,4-dihydro-1H-2-benzothiopyrans (9) with tert-butyl hypochlorite, and subsequent treatment of the 5-membered cyclic aminosulfonium slats (17) with NaOH.