N ‐demethylation of (±)‐6β‐acetoxy‐3‐tropinone. Synthesis of (±)‐6β‐acetoxynortropane | Zendy

He XiaoShu | Zendy; Brossi Arnold | Zendy

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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.

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