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Synthesis of (R)‐(+)‐1,2,3,6‐tetrahydro‐4‐[U‐ 14 C]phenyl‐1‐ [(3‐phenyl‐3‐cyclohexenyl‐1‐yl)methyl]pyridine, a potential antipsychotic agent
Author(s) -
Ekhato I. Victor,
Huang Che C.
Publication year - 1995
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.2580360107
Subject(s) - chemistry , reagent , pyridine , yield (engineering) , cyclohexene , sequence (biology) , stereochemistry , bicyclic molecule , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry , materials science , metallurgy
1,2,3,6‐Tetrahydro‐4‐[U‐ 14 C]phenylpyridine ( 12 ) was synthesized and coupled to (R)‐3‐phenyl‐3‐cyclohexene‐1‐carboxylic acid to make the titled compound 7 in 21% overall yield. Purification considerations were an important factor in the choice of a reaction sequence to 7 , and successful synthesis was facilitated by the superiority of BF 3 .OEt 2 as dehydrating reagent in this system. This otherwise problematic sequence offers an efficient and simple route to compound 7 (PD 143188).