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Syntheses of benzomorphan and related compounds. Part III . An alternate synthesis of 3‐substituted‐1,2,3,4,5,6‐hexahydro‐8‐hydroxy‐2,6‐methano‐6,11‐dimethyl‐3‐benzazocine
Author(s) -
Kametani T.,
Kigasawa K.,
Hayasaka M.,
Wakisaka K.,
Satoh F.,
Aoyama T.,
Ishimaru H.
Publication year - 1971
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570080517
Subject(s) - chemistry , hydrobromic acid , pentazocine , medicinal chemistry , condensation , organic chemistry , medicine , physics , morphine , pharmacology , thermodynamics
Reduction of the appropriate Schiff bases gave 5‐benzylamino‐3‐methyl‐2‐pentene (XVII) and l‐benzylamino‐3‐methylpentane (XVIII), the condensation of which with methyl 3‐(4‐methoxyphenyl)‐2,3‐epoxypropionate afforded a mixture of the isomeric 1‐benzyl‐2‐(4‐methoxy‐benzyl)‐3,4‐dimethyl‐4‐hydroxypiperidines (XIXa and XIXb). The piperidinols were heated with hydrobromic acid, respectively, to afford 3‐benzyl‐1,2,3,4,5,6‐hexahydro‐8‐hydroxy‐2,6‐methano‐6,11‐dimethyl‐3‐benzazocine (II). Since the conversion of II to pentazocine (Ic) had already been accomplished, an alternate synthesis of Ic was achieved.