ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Hofmann exhaustive methylation of the analgesic 1-p-chlorophenethyl-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline (Versidyne = I) leads to 1-dimethylamino-1-(2′-vinyl-4′,5′-dimethoxy-phenyl)-3-(p-chloro-phenyl)-propane (III), the only product formed. Its structure was proved by degradation of the dextrorotatory 1 S enantiomer of Versidyne (Ia) of known absolute configuration, yielding IIIb, the levorotatory 1 S enantiomer of III. Hydrogenation of IIIb affords (-) 1 S 1-dimethylamino-1-(2′-ethyl-4′,5′-dimethoxy-phenyl)-3-(p-chloro-phenyl)-propane (IXb) which was also synthesized by an unambiguous route.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19620450728
