The other, side-issue perhaps, is that I see the MethAmphetamine, Ephedrine, N-methyl-a-methylphenylalanine and N-methyl-a-methylphenylserine as being fairly similar - I don't have chemdraw on this system but most of you will know the structures

(1) MethAmphetamine, Ephedrine, N-methyl-a-methylphenylalanine and N-methyl-a-methylphenylserine all have in common a 3 carbon side chain, with a methylamino group @ C2, with 2 alternative substituents at the stereocenters C1 and C2 (thus R1=OH/H and R2=CO2H or H)

(2) MethAmphetamine, Ephedrine, N-methyl-a-methylphenylalanine and N-methyl-a-methylphenylserine all have a benzylic OH (ie. an OH hanging off the 1-carbon - or the one closest to the ring, so R1 = H or OH)

The methods of accessing them from alanine are "unlikely" (thus the anomalous aside earlier, it is - using Occam's razor - unlikely that with such a relatively simple reaction system so many different mechanisms are (a) possible or (b) necessary) to involve as many different reaction mechanisms as solvent systems/reaction conditions might provide for.

The fact that 3 of these outcomes are possible starting from the N-benzylidenealanine to start with, that all proceed from the a-alkylation of the 2-carbon of the original alanine, the repeated assertions that 5-membered rings have been found by NMR and also the fact that the end products are essentially similar - essentially they are methamphetamine/ephedrine with or without a carboxylic acid substituent @ C2, suggests to me that the various routes might have more in common than is currently imagined, in fact it would be exceedingly implausible that it were not so. To the contrary however, is the fact that this is chemistry, where the implausible is not impossible.

Obfuscation bores the piss out of me, so does "selective quotation" - if you are going to quote something and argue against it, at least have the decency to address the meat of what is actually said, not the minute portion you have chosen to take out of context...

Point 1:

There are 3 routes proceeding from the N-Benzylidene - (i) the "Akabori"* (ii) the "Erlenmeyer" and (iii) the a-alkylation using benzyl halides.

Point 2:

I stated that the existence of 3-4 completely different mechanisms for the preparation of what is essentially the same 3-carbon skeleton from fucking similar starting materials is unlikely. I DID NOT say:

"The methods of accessing them from alanine are "unlikely""

I stated in doing so that my conclusion would be supported by Occam's razor (ie. if you hear hoofbeats, it's probably horses, not zebras). Thus proving that the alternate conclusion - that multifarious reaction mechanisms proceeding from the common point ==> the almost common conclusion (same 3 carbon chain with various substituents @ C1/C2 - actually all proceed the same way - by alkylation of the 2-carbon of the starting alanine), depending upon reaction conditions - was apparently anomalous, thus providing some support for my assertion that attempting to explain the apparently anomalous by recourse to Occam's razor was potentially flawed.**

* I'm still far from convinced that a named reaction could be done using such drastically different reaction conditions - (a) pyridine + heat (Original Akabori - self-evidently highly basic) as opposed to (b) solvent free/melt (the new version) and still retain it's essential character - particularly here where so many reaction mechanisms supposedly exist for the same sortof reaction.

** My suggestion is that there might be something particularly interesting going on - I'm not a chemist, but even I recall reading (repeatedly) that 5-membered rings are favored and some REALLY strange shit can and does happen in order that they may form. If that is the case, look at what would be happening at the original 2-carbon of alanine - it would be quaternary (as it is with the a-alkylation of alanine with benzyl halides), thus that might accelerate decarboxylation given other conditions.

i'm with nicodem on the mechanism hey if you guys think your'e smarter than nicodem dial him up and get him on the topic but after picking this apart meself came to the same conclusion.
occam's razor applies here no magical oxazolidines did you notice they did'nt account for a proton in that mechanism? lying japs yeah!!!

"hey if you guys think your'e smarter than nicodem"

I have agreed with him fully, except for his Occams razor comment. If somehow disagreeing with that means I think I am smarter than him So do we have to take out the rulers and measure?
ps; I dont give a fuck if Nicodems dog is smarter than me;

"However, on many occasions Occam's razor has stifled or delayed scientific progress.[19] For example, appeals to simplicity were used to deny the phenomena of meteorites, ball lightning, continental drift, and reverse transcriptase. It originally rejected DNA as the carrier of genetic information in favor of proteins, since proteins provided the simpler explanation. Theories that reach far beyond the available data are rare, but general relativity provides one example."

"occam's razor applies here no magical oxazolidines did you notice they did'nt account for a proton in that mechanism? lying japs yeah!!!"

No1uno just said everything I wanted to.....

"after picking this apart meself came to the same conclusion."

ROFLMAO, your research obviously did not include googling the words 'Akabori Oxazolidine'.

BTW; I am sure Nicodem would not want you arguing on his behalf as ;
[url]http://www.sciencemadness.org/talk/viewthread.php?tid=5979&page=6[/ur]

In that discussion, he not only says an oxazolidine is formed but briefly talks about the mechanism with No1Uno!!!

Just wanna apologize for opening a new thread on this. I should have looked more carefully for this one.