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Synthesis of ( S )‐1‐(1H‐indol‐4‐yloxy)‐3‐[4‐(3‐methoxyphenyl)‐4‐hydroxypiperidin‐1‐yl]‐propan‐2‐ol (LY333068) succinate, and its 3‐[ 14 C]‐isotopomer based on chiral glycerol‐[ 14 C] derivatives
Author(s) -
Czeskis Boris A.
Publication year - 1998
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199806)41:6<465::aid-jlcr103>3.0.co;2-b
Subject(s) - chemistry , yield (engineering) , diol , isotopomers , dioxolane , stereochemistry , decarboxylation , deamination , bicyclic molecule , medicinal chemistry , catalysis , organic chemistry , materials science , molecule , metallurgy , enzyme
The 3‐[ 14 C]‐isotopomer of ( S )‐1‐(1H‐indol‐4‐yloxy)‐3‐[4‐(3‐methyoxyphenyl)‐4‐hydroxypiperidin‐1‐yl]‐propan‐2‐ol (LY333068), a 5HT 1A antagonist, was prepared in 10 steps and 8.2% radiochemical yield from ( L )‐serine‐[3‐ 14 C]. Deamination, esterification, and protection of the resulting diol gave methyl ( R )‐2,2‐dimenthyl‐1,3‐dioxolane‐4‐carboxylate‐[3‐ 14 C], as a chiral and radiolabeled building block, which then was subsequently coupled with 4‐hydroxyindole and 4‐(3‐methoxyphenyl)‐4‐hydroxypiperidine to give the titled product with 99.4% radiochemical purity. © 1998 John Wiley & Sons, Ltd.