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14C-labeled antimalarials. I. Synthesis of dl-erythro- and threo-α(2-piperidyl)-2,8-bis(trifluoromethyl)-4-quinolinemethanol-α-14C

✍ Scribed by William H. Yanko; George F. Deebel

Publisher
John Wiley and Sons
Year
1980
Tongue
French
Weight
291 KB
Volume
17
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Erythro‐ and threo‐ isomers of α‐(2‐piperidyl)‐2,8‐bis‐(triflucoromethyl)‐4‐quinolinemethanol‐α‐^14^C hydrochloride and methanesulfonate were prepared from labeled carbon dioxide for metabolic and pharmacological studies. Intermediates were 2,8‐bis(trifluoromethyl) cinchoninic‐carboxy‐^14^C acid and 2,8‐bis(trifluoromethyl)‐4‐quinolyl 2‐pyridyl ketone‐^14^C. The ratio of erythro to threo isomers formed on hydrogenation of the precursor ketone was 5.6. The diastereomers were separated by recrystallization and preparative tlc. Erythro‐to‐threo conversion was effected by isomerization of the acetylated erythro isomers and deacetylation.

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✍ Ying-Tsung Lin; M. A. Leaffer; Masato Tanabe 📂 Article 📅 1976 🏛 John Wiley and Sons 🌐 French ⚖ 415 KB

## Abstract The ring‐ and side‐chain‐^14^C‐labeled DL‐4,4′‐propylenedi‐2,6‐piperazinediones (I) were synthesized from chloroacetic acid‐1‐^14^C in two steps and from DL‐analine‐1‐^14^C in six steps, respectively. The radiochemical yield for the ring labeling was 24.5%; for the side‐chain labeling i