KingJacksonV (Stranger)
08-16-01 17:31
No 205283
      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
 
 
 
 
    Osmium
(Stoni's sexual toy)
08-16-01 17:49
No 205291
      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.
 
 
 
 
    hypo
(Hive Bee)
08-17-01 01:29
No 205382
      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.
 
 
 
 
    b159510
(Professional Student)
08-17-01 09:11
No 205420
      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
 
 
 
 
    jim
(Hive Bee)
08-17-01 12:17
No 205460
      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