The practical synthesis of (2S)-7-methoxy-1,2,3,4-tetrahydro-2-naphthylamine via optical resolution of 2-(3-methoxybenzyl)succinic acid.
We describe the practical synthetic route for (2S)-7-methoxy-1,2,3,4-tetrahydro-2-naphthylamine 1(2S)-2-amino-7-methoxytetraline; (S)-AMT]. (2R)-2-(3-Methoxybenzyl)succinic acid [(R)-1] was obtained by the optical resolution of 2-(3-methoxybenzyl)succinic acid (1) as the salt of (1R,2S)-2-(benzylamino)cyclohexylmethanol (7), and (R)-1 was converted to the optically active (2S)-7-methoxy-1,2,3,4-tetrahydro-2-naphthoic acid [(S)-2] by the intramolecular Friedel-Crafts reaction followed by catalytic hydrogenation. (S)-AMT was obtained from the acid (S)-2 by Hofmann rearrangement without racemization.
Yanagi
T
T
Central Research Laboratories, Kissei Pharmaceutical Co., Ltd., Minamiazumi, Nagano, Japan. takashi_yanagi@pharm.kissei.co.jp
Kikuchi
K
K
Takeuchi
H
H
Ishikaw
T
T
Nishimura
T
T
Kamijo
T
T
Yamamoto
I
I
D000318:Adrenergic beta-Agonists / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000494:pharmacology*; D009904:Optical Rotation; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
C430811:(2)-7-methoxy-1,2,3,4-tetrahydro-2-naphthylamine; D000318:Adrenergic beta-Agonists; D009281:Naphthalenes