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Synthesis of R-(+)- and S-(−)-8-hydroxy-2-(N, N-dipropylamino)-[2-3H] tetralin. HCl (8-OH-DPAT) a 5HT1A receptor agonist

✍ Scribed by M. J. Ackland; L. G. Dring; J. R. Jones; N. Gilon

Publisher: John Wiley and Sons
Year: 1991
Tongue: French
Weight: 364 KB
Volume: 29
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580290807

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✦ Synopsis

Abstract

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.

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