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Synthesis of 14 C‐labeled S‐(‐)‐1‐phenylethylamine and its application to the synthesis of [ 14 C] CI‐1021, a potential antiemetic agent (1)
Author(s) -
Zhang Yinsheng
Publication year - 2000
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 - 10.1002/1099-1344(20001015)43:11<1087::aid-jlcr394>3.0.co;2-7
Subject(s) - chemistry , acetophenone , stereochemistry , oxime , ring (chemistry) , enantiomer , enantioselective synthesis , amine gas treating , indole alkaloid , enantiomeric excess , yield (engineering) , ether , medicinal chemistry , indole test , organic chemistry , catalysis , materials science , metallurgy
S‐(‐)‐1‐[U‐ring‐ 14 C]phenylethylamine 3 was synthesized through the enantioselective borane reduction of E‐[U‐ring‐ 14 C]acetophenone oxime methyl ether derived from [U‐ring‐ 14 C]acetophenone. The overall radiochemical yield was 66.7%. The enantiomeric excess (ee) was 96.60%. Coupling the labeled amine 3 with (R)‐N‐[(benzo[b]furan‐2‐ylmethoxy)‐carbonyl‐2‐methyltryptophan 4 provided [R‐(R * ,S * )]{1‐(1H‐indole‐3‐ylmethyl)‐1‐methyl‐2‐oxo‐2‐[(1‐[U‐ring‐ 14 C]phenylethyl) amino]ethyl} carbamic acid benzo[b]furan‐2‐ylmethyl ester (CI‐1021), a potential antiemetic agent. Copyright © 2000 John Wiley & Sons, Ltd.