Premium
The synthesis of the 14 C and 2 H‐isotopomers of ( R )‐N‐[2‐(2′‐ethoxyphenoxy)‐ethyl]‐N‐2‐[3‐(4′‐methoxy‐3′‐sulfonamido)‐phenyl]‐propylamine hydrochloride, an α 1 ‐adrenoreceptor antagonist
Author(s) -
Wheeler William J.,
Schmiegel Klaus K.,
Hunden David C.
Publication year - 1989
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/jlcr.2580270207
Subject(s) - chemistry , isotopomers , reductive amination , propylamine , yield (engineering) , catalysis , medicinal chemistry , chemical synthesis , organic chemistry , biochemistry , materials science , amine gas treating , molecule , metallurgy , in vitro
The synthesis of [ 14 C]‐ and [ 2 H]‐labeled LY253351 (YM12617–1), a potent α 1 ‐receptor antagonist, which is potentially useful in the treatment of benign prostatic hypertrophy (BPH) is described. The [ 14 C]‐isotopomer was synthesized from [ 14 C]‐potassium cyanide in nine steps in 1.5% radiochemical yield. One of the key intermediates, [ 14 C]‐4‐methoxyphenylacetone, was synthesized from [ 14 C]‐4‐methoxyphenylacetyl chloride by a Pd(0)‐catalyzed reaction with tetramethylstannane. The [ 2 H]‐labeled material was synthesized by a Pd/C catalyzed reductive amination with deuterium gas.