Premium
Synthesis of R‐(+)‐ and S‐(−)‐8‐hydroxy‐2‐(N, N‐dipropylamino)‐[2‐ 3 H] tetralin. HCl (8‐OH‐DPAT) a 5HT 1A receptor agonist
Author(s) -
Ackland M. J.,
Dring L. G.,
Jones J. R.,
Gilon N.
Publication year - 1991
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.2580290807
Subject(s) - chemistry , tetralin , agonist , stereochemistry , 5 ht receptor , 8 oh dpat , medicinal chemistry , receptor , serotonin , organic chemistry , catalysis , biochemistry
The title compounds were synthesised in 7 steps from 1,7‐dihydroxynaphthalene as follows: 1,7‐dihydroxynaphthalene was methylated and subjected to a Birch reduction to yield 8‐methoxy‐2‐tetralone. Reductive amination with sodium cyanoboro[ 3 H]hydride and n‐propylamine gave 8‐methoxy‐2‐(n‐propylamino)‐[2‐ 3 H]tetralin which was acylated and reduced to give (±) 8‐methoxy‐2‐(N, N‐dipropylamino)‐[2‐ 3 H]tetralin. Treatment with conc. HCl gave (±)‐8‐hydroxy‐2‐(N, N‐dipropylamino)‐[2‐ 3 H]tetralin. The racemate was then resolved by chiral mobile phase chromatography.