12-21-03 10:58
No 478216
I have a few questions related to the synthesis of dextromethorphan. I've tried searching the site, but without satisfying results.
The only description of DXM's synthesis I've found is that of converting 1,2,3,4,5,6,7,8-octahydro-1-(4-methoxybe
First of, does anyone know any other routes to dextromethorphan?
Second of, if one has racemethorphan, is it possible to separate the two isomers using l-tartaric acid? That would convert the levomethorphan into it's tartaric salt leaving the dextromethorphan in the solution, wouldn't it?
I apologize if my questions seem a bit "noobish", my knowledge about stereo chemistry is quite limited, but hey, at least I'm learning new things all the time. :D
Love!
(Chief Bee)
12-21-03 12:47
No 478238
(Rated as: good read)
Racemorphan stereoisomer separation into levo/dextro-methorphan with L-tartaric acid:
Patent US2676177
Patent DE840242
I have also found one stereoselective synthesis which does not produce the scheduled levo-isomer, but only dextromethorphan:
General asymmetric synthesis of benzomorphans and morphinans via enantioselective hydrogenation
M. Kitamura, Yi Hsiao and R. Noyori, H. Takaya
Tetrahedron Letters 28(41) , 4829-4832 (1987)
DOI:10.1016/S0040-4039(00)96636-X
Abstract
A variety of optically active benzomorphans including metazocine and pentazocine as well as dextromethorphan, a morphinan, are obtainable by using the BINAP-ruthenium(II) catalyzed enantioselective hydrogenation as key operation.
The Hive - Clandestine Chemists Without Borders