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All 2 posts Subject: Questions about the synthesis of dextromethorphan Please login to post Down

Ezaey
(Stranger)
12-21-03 18:58
No 478216
      Questions about the synthesis of dextromethorphan

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-methoxybenzyl)isoquinoline to the corresponding morphinan using Grewe's cyclization, but I have a couple of questions.

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!

Rhodium
(Chief Bee)
12-21-03 20:47
No 478238
User Picture       Synthesis of Dextromethorphan
(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}

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	All 2 posts		Subject: Questions about the synthesis of dextromethorphan		Please login to post		Down


		Ezaey (Stranger) 12-21-03 18:58 No 478216				Questions about the synthesis of dextromethorphan
						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-methoxybenzyl)isoquinoline to the corresponding morphinan using Grewe's cyclization, but I have a couple of questions. 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!



		Rhodium (Chief Bee) 12-21-03 20:47 No 478238				Synthesis of Dextromethorphan (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}

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