Thread: How to prepare alanine

I am interested in preparing alanine following the strecker synthesis which uses acetaldehyde, ammonium chloride, sodium cyanide and Hydrochloric acid. However I cannot find a source/ a procedure on how to do so. My question is how would I go about finding this information. Thank you for responding.

Originally Posted by 96747

I am interested in preparing alanine following the strecker synthesis which uses acetaldehyde, ammonium chloride, sodium cyanide and Hydrochloric acid. However I cannot find a source/ a procedure on how to do so. My question is how would I go about finding this information. Thank you for responding.

I'm afraid I can't help much. The only book I have on organic synthesis does not go into the details of the procedures. There are numerous references in the various web articles about the Strecker synthesis. And I did find this website on organic syntheses which may get you on the right track: http://www.orgsyn.org/Content/pdfs/p...s/CV1P0021.pdf

Good luck.

Originally Posted by 96747

I am interested in preparing alanine following the strecker synthesis which uses acetaldehyde, ammonium chloride, sodium cyanide and Hydrochloric acid. However I cannot find a source/ a procedure on how to do so. My question is how would I go about finding this information. Thank you for responding.

Using the original Strecker synthesis gives a racemic mixture of various amino acids (i.e. 50:50 D and L stereoisomers). An adaptation allows for "Asymmetric Strecker reactions", providing chiral compounds.

If you don't find what you are looking for in the reference from exchemist, try the below link. It might provide some insight, in addition to other references that might help.

Just out of curiosity, why do you want to synthesize alanine?


https://en.wikipedia.org/wiki/Streck...acid_synthesis

Originally Posted by Double Helix

Originally Posted by 96747

I am interested in preparing alanine following the strecker synthesis which uses acetaldehyde, ammonium chloride, sodium cyanide and Hydrochloric acid. However I cannot find a source/ a procedure on how to do so. My question is how would I go about finding this information. Thank you for responding.

Using the original Strecker synthesis gives a racemic mixture of various amino acids (i.e. 50:50 D and L stereoisomers). An adaptation allows for "Asymmetric Strecker reactions", providing chiral compounds.

If you don't find what you are looking for in the reference from exchemist, try the below link. It might provide some insight, in addition to other references that might help.

Just out of curiosity, why do you want to synthesize alanine?


https://en.wikipedia.org/wiki/Streck...acid_synthesis

I think our friend will have been able to find the Wiki article.

Originally Posted by exchemist

Originally Posted by Double Helix

Originally Posted by 96747

I am interested in preparing alanine following the strecker synthesis which uses acetaldehyde, ammonium chloride, sodium cyanide and Hydrochloric acid. However I cannot find a source/ a procedure on how to do so. My question is how would I go about finding this information. Thank you for responding.

Using the original Strecker synthesis gives a racemic mixture of various amino acids (i.e. 50:50 D and L stereoisomers). An adaptation allows for "Asymmetric Strecker reactions", providing chiral compounds.

If you don't find what you are looking for in the reference from exchemist, try the below link. It might provide some insight, in addition to other references that might help.

Just out of curiosity, why do you want to synthesize alanine?


https://en.wikipedia.org/wiki/Streck...acid_synthesis

I think our friend will have been able to find the Wiki article.

I'm curious as to where our friend is getting sodium cyanide. If this is to be done at a university chemistry laboratory, then our friend should have access to the chemistry literature.

Originally Posted by KJW

I'm curious as to where our friend is getting sodium cyanide. If this is to be done at a university chemistry laboratory, then our friend should have access to the chemistry literature.

That is a very good question, and got me thinking about what this is all about. Students would also have professors to instruct them on means of getting such information.

Now I am not suggesting that 96747 is planning on doing anything illegal.

But if you get the starting ingredients far enough back in the synthetic scheme, you might be able to pull this off without a lot of attention. And looking up too much stuff on the internet might leave a trail you don't want people to follow (e.g. Wiki links, etc.)

N-methylation of alanine, a pretty simple reaction, yields N-methylalanine, one of two precursors for synthesis of ephedrine (1, 2). Ephedrine is used in the synthesis of methamphetamine. There is still the matter of racemic alanine products to be considered (but can be circumvented with directed chemistry). But that might not matter if only 50% of the product is active (and the other 50% is not toxic). There could be other chiral centers, have not run all this down.

While 96747 may have other alternatives, it is pretty clear that ephedrine, which is hard to come by (in bulk) for obvious reasons, can be made from simpler compounds, if you have the chemicals and know what to do.

Again, if you start far enough back, you might not get any attention (3). But would 96747 be doing that?

You wouldn't do that, would you 96747?! The absence of an answer may provide an answer in itself. Time may, or may not, tell us.



"Profiling ephedrine prepared from N-methylalanine via the Akabori-Momotani reaction "

1. https://pubmed.ncbi.nlm.nih.gov/28658566/



"Detailed investigations into the Akabori–Momotani reaction for the synthesis of amphetamine type stimulants: Part 2 [2018] "

2. https://agris.fao.org/agris-search/s...US201900107370



"The DARK Side of Total Synthesis: Strategies and Tactics in Psychoactive Drug Production"

3. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6205722/

Originally Posted by 96747

I am interested in preparing alanine following the strecker synthesis which uses acetaldehyde, ammonium chloride, sodium cyanide and Hydrochloric acid. However I cannot find a source/ a procedure on how to do so. My question is how would I go about finding this information. Thank you for responding.

A search of chemicals used in the synthesis of illicit methamphetamine and related compounds references the use of N-methyl-DL-alanine as a definite component. None of these references will be provided in this post for obvious reasons. The racemic mix of the D and L forms of alanine is expected from the "strecker synthesis".

Since we have not heard back from our friend asking more about the synthesis of alanine, one can only wonder what the individual is up to.

BTW, the number 96747 is the zip code for Kauai County, Hawaii. If that is where our friend is, it sure would be a nice place to conduct organic synthesis for whatever one is after!