In an extension of this work, Schnider and his colleagues condensed the salt (36) with the Grignard reagent from p-methoxy-benzyi chloride. The product (40), on reduction (41) and cycliza tion, affords the methoxylated morphinan (41). Removal of the methyl ether affords the narcotic analgesic racemorphan (43)  [c.293]

As an alternate route to functionalized morphinans, the intermediate, 38, is first nitrated, the group entering para to the methylene bridge (44). Reduction of the nitro to the aniline (45) followed then by diazotization and replacement by hydroxyl gives intermediate, 46. Cyclization as above again gives racemorphan.  [c.293]

Resolution of racemorphan via the tartrate salt affords a very potent analgesic. The (-) isomer, is a narcotic  [c.293]

See pages that mention the term Racemorphan : [c.836]    [c.435]    [c.444]    [c.276]    [c.245]   
The organic chemistry of drug synthesis Vol.1 (1977) -- [ c.293 ]