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An Alternative Synthesis of the Dopaminergic Drug 2-Amino-1,2,3,4-tetrahydronaphthalene-5,6-diol (5,6-ADTN)

✍ Scribed by Süleyman Göksu; Hasan Seçen; Yaşar Sütbeyaz

Publisher
John Wiley and Sons
Year
2006
Tongue
German
Weight
67 KB
Volume
89
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Racemic 2‐amino‐1,2,3,4‐tetrahydronaphthalene‐5,6‐diol (5,6‐ADTN; 4) was synthesized from 5,6‐dimethoxynaphthalene‐2‐carboxylic acid (14) in four steps (60% overall yield; Scheme). The crucial steps of the synthesis are Birch reduction of 14 to the valuable synthon 15, Curtius reaction and carbamate formation (16), hydrogenolysis (17), and demethylation to the biologically active hydrobromide salt 18 of 4.

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