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Lactams. XXIV. Alkaline hydrolysis of 1-benzyl-2-piperidone derivatives: application to cis-trans isomerization of the 5-ethyl-2-oxo-4-piperidineacetic acid system Fujii, Tozo 60115219 Ohba, Masashi Akiyama, Shigeaki In boiling 2.5 N solution of KOH in 40% (w/w) aqueous EtOH, the lactams (±)-5a, b, d were hydrolyzed to an extent of 75-98% within 8-20 h, attaining equilibrium with the corresponding ω-amino acid derivatives (±)-6a, b, d. The potassium salt (±)-8,generated in situ from the translactam acid (±)-7,was equilibrated with the ring-opened product (±)-6f and the recyclized cis isomer (±)-5f in a ratio of 57 : 15 : 28 within ca. 45 h under similar reaction conditions. The cis-N-(2-arylethyl) analog (-)-9 was converted into the trans-lactam acid (+)-13,a key synthetic precursor for the 8-hydroxy-9,10-dimethoxybenzo [a] quinolizidine-type Alangium alkaloids, through application of such alkaline hydrolytic cis-trans equilibration followed by debenzylation. 日本薬学会 1985-04-25 2017-10-03 eng journal article VoR http://hdl.handle.net/2297/7627 https://kanazawa-u.repo.nii.ac.jp/records/14780 10.1248/cpb.33.1716 AA00602100 0009-2363 Chemical & pharmaceutical bulletin 33 4 1716 1720 https://kanazawa-u.repo.nii.ac.jp/record/14780/files/PH-PR-OHBA-M-1716.pdf application/pdf 605.1 kB 2017-10-03