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Report | Regular issue | Vol 19, No. 11, 1982, pp.2109-2114
Published online, 1st January, 1970
DOI: 10.3987/R-1982-11-2109
Byproducts in the O-Phenyltetrazolylation of (±)-2,4-Dihydroxy-N-formylmorphinan-6-one. Alkylation at C-5

Fu-Lian Hsu, Kenner C. Rice, and Arnold Brossi

*Section of Medicinal Chemistry, Laboratory of Bioorganic Chrmistry, NIDDK, National Institute of Health, Bethesda, MD 20892, U.S.A.


O-Alkylation of (±)-2,4-dihydroxy-N-formylmorphinan-6-one (4) with 5-chloro-1-phenyl-1H-tetrazole in DMF in the presence of potassium carbonate afforded substantial amounts of the C-5 alkylated ketones 6 and 7 in addition to the desired ketone 5. The structures of 5, 6 and 7 were supported by chemical correlation and on the basis of spectral data.