ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Syntheses of the Analgesic 2-[1-(m-Methoxyphenyl)-2-cyclohexen-1-yl] -N,N-dimethyl-ethylamineThree principal routes to 2-[1-(m-methoxyphenyl)-2-cyclohexen-1-yl]- N,N-dimethyl-ethylamine (13), a compound with interesting analgesic properties, are described. In the first, derivatives of [1-(m-methoxyphenyl)-2-cyclohexen-1-yl]acetic acid (10) (alternatively the ethyl ester 29, the dimethylamide 32 or the nitrile 34) serve as crucial intermediates. All three can be synthesized from 2-(m-methoxyphenyl)cyclohexanone (1) by sequences comprising successively C-alkylation (1→2,4,5; Scheme 1), reduction of the ketone carbonyl group (2→6;4→18;5→19; Scheme 1 and 2) and elimination (16→29; 18→32; 19→34; Scheme 2). The relative configuration of the cyclohexanols 16, 18, 19 and of a series of related compounds is established by chemical correlation with the lactone 30 the structure of which follows from 1H-NMR. data (Scheme 2). The second route creates the intermediates 29 and 32 by ester- or amide-enolate-Claisen-type-rearrangement reactions starting from 3-(m-methoxyphenyl)-2-cyclohexen-1-ol (39; Scheme 3). Compounds 29, 32 and 34 are transformed into the target molecule 13 by standard reactions. A Hofmann elimination of the quaternary ammonium fluoride 50 (X=F), derived from the known cis-perhydroindoline 48, is the essential step in the third approach to 13 (Scheme 4).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19830660217
