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

• Published in: Helvetica chimica acta Vol. 89; no. 2; pp. 270 - 273
• Main Authors: Goksu, S, Secen, H, Sutbeyaz, Y
• Format: Journal Article
• Language: English
• Published: Zürich WILEY-VCH Verlag 01.02.2006; WILEY‐VCH Verlag; Wiley
• Subjects: 2-amino-1; 4-tetrahydro-; 6-ADTN; 6-dimethoxy; 6-diol; Chemistry; Chemistry, Multidisciplinary; Dopamin; Dopaminergic drug; Naphthalene-2-carboxylic acid; Naphthalene-5; Naphthalene‐2‐carboxylic acid, 5,6‐dimethoxy; Naphthalene‐5,6‐diol, 2‐amino‐1,2,3,4‐tetrahydro‐ (5,6‐ADTN); Physical Sciences; Science & Technology; ACID; CONCISE SYNTHESIS; DERIVATIVES; AGONIST
• ISSN: 0018-019X; 1522-2675
• DOI: 10.1002/hlca.200690030

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.