ChemicalSolution (Hive Bee)
03-08-02 09:27
No 278820
      alanine and Akabori???  Bookmark   

From this extract, SWIM isn't so sure that PPA can be made by heating bezh with alanine.....

The Akabori reaction (I) (C.A. 41, 3774g) on BzH and dl-MeCH(NHMe)CO2H (II) with and without pyridine and removal of the unreacted BzH by steam distn. gave dl-ephedrine and dl-y-ephedrine.  Similarly, direct heating of piperonal and II gave 2 dl-1-(3,4-methylenedioxyphenyl)-2-methylamino-1-propanols. A new reaction (III), differing from I, takes place on heating BzH and DL-alanine directly; PhCH2NH2, PhCH(OH)CHPhNH2 (2 dl-compds.), AcH, and CO2 are formed.  It is considered that the I-type reaction occurs when the N of the amino acid is secondary and the III-type reaction when it is primary.

What the heck is PhCH(OH)CHPhNH2 anyway? 1,2 biphenyl, ethanolamine?  Or--- is this a mistake?  And what is Ach?

Is there any evidence that the Akabori reactin will work with (non-N-methylated) alanine??

Aside--- N-methyl alanine could be made from 2-Br-propionic acid by the SN2 displacement by methylamine.  The 2-bromopropionic acid is made easily from alanine (SWIM knows this one for sure).  Whew.. This is getting to be a lot of work..

(Distinctive Doe)
03-08-02 11:26
No 278876
      Re: alanine and Akabori???  Bookmark   


I think it may bee benzoin with an amine in place of the ketone.  Or kinf of like and ephedrine molecule where the last carbon on the propyl chain is replaced with an aromatic ring(no N-methyl either)

Here is benzoin

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