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N ‐demethylation of (±)‐6β‐acetoxy‐3‐tropinone. Synthesis of (±)‐6β‐acetoxynortropane
Author(s) -
He XiaoShu,
Brossi Arnold
Publication year - 1991
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.5570280716
Subject(s) - chemistry , demethylation , decarbonylation , tetrahydrofuran , acetic acid , amine gas treating , organic chemistry , carbamate , zinc , medicinal chemistry , catalysis , biochemistry , gene expression , solvent , dna methylation , gene
Nortropinone 5 , prepared from 3 by N ‐demethylation with trichloroethyl chloroformate, followed by deprotection of carbamate 4 with zinc in acetic acid, served as a starting material to prepare the N ‐protected 6‐acetoxy ketones 7 and 9–12 , and alcohols 6 and 8 . Nortropane 16 was prepared from 3 by decarbonylation via dithioketal 13 followed by N ‐demethylation, and from 10 by decarbonylation via dithioketal 14 . When ethanol was used in the desulfurization of 14 instead of tetrahydrofuran, substantial amounts of the N ‐ethylated amine 17 were produced.