Phenylalanine to the Alkane Amine

java · Consumer

Phenylalanine conversion to alkane-amine has long been a goal from many research getto chemists as far back as the first Hive with members like cherrie baby, Drone, Hellman, Chemguy, Rhodium,and the list goes on.

More recently there has been some methods that are easier on the reduction of the amino acid to the amino alcohol,NaBh4/I, NaBH4/H2SO4,NaBH4/Ni/H2O where the road seems to get narrow .

There has been suggested that the RP/HI, a well known procedure, would work on this primary non-benzylic alcohol would work , but the verdict is still out . There has been some attempts in reduction of the OH to a halogen , by using non-thionyl chloride nor Phosphorous halides, as they are difficult to get, but there has been no reported success thus far.

The suggestion of a tosylating the alcohol then this would make it a much easier leaving group, but the method to remove this easier leaving group has not been made clear to me ....read this thread,
http://www.wetdreams.ws/forum/topic.asp?TOPIC_ID=3986

So this is were I've read the situation rests , in addition some have mention of reading biotransformation of the starting amino acid to the phenylalaninol, but this researcher has not read it nor knows of its name or journal were it appeared.

There are many suggestions and other methods which were recorded in a long thread that was kept going , but not available at this time , but will try to post it...........java

java · Consumer

This is one of the best methods I've found to make the amino alcohol from the amino acid, without the need of THF or any exotic solvents......java
------------------------------------------------------------------------------------
Transition Metal Compound Mediated Reduction of
-Amino Acids to 1,2-Amino Alcohols with NaBH4 in
Water
Ayhan S. DEM_IR, _Idris M. AKHMEDOV, ®O. S ES ENO GLU

Turk J. Chem. (1999),23,2123-126

PDF

Abstract
A new efficient and cost-effective method for the preparation of 1,2-amino alcohols is described.
The reactions of amino acids with NaBH4 in the presence of NiCl 2 or MoO3 in water give 1,2-amino alcohols in high yield. When optically pure amino acids were used, optically pure 1,2-amino alcohols were obtained.

Note The hosting ripway only allows 3MB per day download so if not able to download wait 24hrs then download...sorry this is the best I can do being that this forum doesn't have upload features.....java

Guest · Tue Feb 08, 2005 3:10 am

Good Post: And informative read,
It is such an elegant pathway,

Yes Phenylanaline has a good many uses:

Phenylanaline (ppa)+heat--> Pea(Phenylethyamine

Is prepared by boiling in suitable high temp solvent,

Doing a double Mannich, (formaldehyde,acetone,PEA)
forms PhenylethylPiperidine"NPP"

This was where we got up to........

With such a readily available precursor, more effort should be posted

PEA+Methyl Acrylate(cyclization)----->NPP

Synthekkman- hell what a day!

java · Consumer

I saved the thread on the persuit as well as all the references mentioned in the archives which I can upload whenever there is a place to upload to............java

Phenylalanine to Phenylalaninol Archives

Guest · Tue Feb 08, 2005 7:07 am

Ok, Java,

You have permission to collect the entire post from the hive, and format it, into a post here in this forum,.

Make it a nice looking post, at then we can all continue on,.

I'll pm you about some other stuff you might like,

cheers
syn

Guest · Tue Feb 08, 2005 7:37 am

Ok, A kind member has given us all here a home for all our files,

It should only be a day or so,

So for now, find all the files, if you don't want to repost them, and pm me the links, and as soon as we can, an upload area will be created,

If you personally want access to the FTP site, you will have to pm me,.

Seeya

syn

Guest · Tue Feb 08, 2005 8:35 am

Here it is
http://12.162.180.114:90/synthetika/phenylalaninetoamphcontinuation9-04.htm

Thankyou to The Watcher, for his kind server space!
syn

Guest · Thu Feb 10, 2005 8:00 am

The way to do this is:
1) React phenylalanine with benzophenone
2) Alpha-methylate the reaction product
3) Split off the benzophenone to obtain alpha-methyl-phenylalanine
4) Decarboxylate this to obtain amphetamine

java · Consumer

Guest · Sat Feb 12, 2005 11:26 pm

PhenylethylPiperidine what this chemical look like? Whats it more IUPC aceptable name?

CherrieBaby · chouchou

java · Consumer

Although I recognize the method of making esters as a clean route , the problem arises with obtaining material OTC. The reason to follow the Phenylalanine to Phenylalaninol to an alkane is because getting to the Phenylalaninol seems easier and especially with the study of doing it in water and NaBH4 at RT.

The second part has been a challenge as it was in the early days of the Hive board as read in the documented archives. Although Labrat once posted that Assholium had shown the RP/HI worked well in reducing it to the alkane. However, that thread or specifics were never found or documented in any archives tha can be found.

In going to the chlorinated phenylalaninol, what is the name of this compound and its solubilities, by the ZnCl + HCl , for lack of a better method, the de-halogenation there is no problem to get to the alkane from here.

However it would be nice to know some of the physical properties of the chlorinated phenylalaninol , starting with it's name , so it can be separated from the zinc chloride after the chlorination..........java

mannich_depression · Tue Mar 22, 2005 12:20 pm

CherrieBaby,

What other carbonyl compounds can be used in place
of benzophenone?

M_D

java · Consumer

Well it seems that the chlorinated phenylalaninol, the alcohol of phenylalanine, name is......as WixardX over at WD posted as follows,

mk-1 · Fri Apr 08, 2005 4:55 am

thought id drop by and contribute my little part :
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Efficient Procedure for the Reduction of -Amino Acids to Enantiomerically Pure -Methylamines
Dominick A. Quagliato, Patrick M. Andrae, and Edward M. Matelan
J. Org. Chem.; 2000; 65(16) pp 5037 - 5042
DOI: 10.1021/jo000242h
pdf

cant retrieve the article right now cause ACS is giving me problems, but ill try on. if anyone else can retrieve it, then i think this is a valid way Smile

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Note: the citation has been placed in the journal citations archives in the reference section and here as a pdf, thanks to nubee....java