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D-stereoisomer to racemic mixture

adder

adder

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Mar 28, 2006
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Is it possible to make a racemic mixture of two isomers having one isomer? If so, how? The process called racemization can been seen in Datura Strammonium where in dried leaves l-hyoscyamine racemizates to atropine. But we've got a pure chemical here.
 
It depends which chemical you're talking about. Some can be. Many others cannot (in practical, realistic terms).
 
adder said:
Is it possible to make a racemic mixture of two isomers having one isomer? If so, how? The process called racemization can been seen in Datura Strammonium where in dried leaves l-hyoscyamine racemizates to atropine. But we've got a pure chemical here.
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Can you get me the chemical structures or IUPAC with stereochemistry for both of those drugs? I'd be happy to find you a mechanism for the racemization (from which we could probably tell how readily it is reversible), but the structures I've tracked down are wrong or incomplete, and I'm feeling too lazy to look them up in Merck.
 
I don't think the OP has mentioned which substance he wants to raceamize, I suspect like most of these questions it will be a certain N substituted alpha alkyl phenethylamine....:\

basically in order to racemize something it must be converted to a non chiral intermediate.
 
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Oh, I thought he wanted the mechanism for hyoscyamine -> atropine racemization, and wanted to know if this could be reversed.
 
sure, if L-methamphetamine was a realistic possibility it wouldn't be available OTC
 
perhaps the original poster would like to enlighten us as to which chemical he is dreaming about, if it is dxm to levomethorphan it is impossible, if it is l meth to d meth then it is possible but not very easy.

until then I think this thread is going nowhere.
 
^^
I would tend to say the opposite, most additions are non-specific, hense the need for inorganic, stereospecific catalysts or biological synthesis.
 
adder said:
I wanted racemethorphan/levomethorphan from DXM. :(
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sadly that is almost impossible, the difference between the two is that the nitrogen containing ring sticks out on different sides from the flattish rest of the molecule. the only way to do it would be to break that ring at the nitrogen and re-attach it on the other side. not really possible :(

it would be quicker and easier to make it racemethormorphan from scratch.

where it is just a matter of changing one chiral centre by inversion or whatever then that is doable. when that chiral centre is attached to another chiral centre then things become very complex.
l meth to racemic meth is theoretically possible using the enamine, or the imine as an intermediate.

V
 
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