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KingJacksonV
(Stranger) 08-16-01 17:31 No 205283 |
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Li/NH3 enantiomeric questions | Bookmark | |||||
Hey guys, I wondered if you could clear something up for me. I keep hearing the use of psudoephedrine as a precursor in the Birch rxn. I thought reduction of a benzyl alchol via "Birch" yields 99.8 percent straight conversion from one enantiomer of ephedrine to the corresponding+/- enantiomer of N-methyl amphetamine, unracemized (JACS reduction of benzy;). If this is true, then wouldn't SWIM get active product if he were to start with the + ephedrine salt, instead of the pseudo? I'll sleep when I'm dead |
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Osmium (Stoni's sexual toy) 08-16-01 17:49 No 205291 |
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Re: Li/NH3 enantiomeric questions | Bookmark | |||||
I'm kinda confused about the chiralities of ephedrines and pseudoephedrines right now. But I think the reason is the following: ephedrine and pseudoephedrine have TWO chirality centers, the benzylic position and the carbon to which the amine functionality is connected. When doing a Birch you reduce the benzylic OH, and this chirality center disappears, and only one is left. |
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hypo (Hive Bee) 08-17-01 01:29 No 205382 |
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Re: Li/NH3 enantiomeric questions | Bookmark | |||||
yep, pseudoephedrine and ephedrine differ on the -OH carbon. both should give the good stuff. Man was not born to work. |
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b159510 (Professional Student) 08-17-01 09:11 No 205420 |
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Re: Li/NH3 enantiomeric questions | Bookmark | |||||
wouldn't SWIM get active product if he were to start with the + ephedrine salt, instead of the pseudo? ..I believe you will be needing (-)ephedrine. Back to the Primitive |
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jim (Hive Bee) 08-17-01 12:17 No 205460 |
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Re: Li/NH3 enantiomeric questions | Bookmark | |||||
This is in the search engine. I have posted the correct answer several times. d-psuedoephedrine yeilds d-meth l-ephedrine yields d-meth l-psuedo yeilds l-meth d-ephedrine yields l-meth |
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