Phenylalanine to the Alkane Amine

64bandil · Busy Bee

I suggested the use of titanocene dichloride back at TH some time ago. Any final verdict on that one?

It's able to reduce carboxylic esters directly to the alkane and the alcohol:

RCOOR´ + (C₅ H₅ )₂ TiCl₂ --> RCH3 + R´OH¹

Another method is presented here:

java · Consumer

64bandil .......thanks for reminding me of that as I completely forgot since I was trying to complete the reduction of phenylalanine to the alkane with OTC material or at least some of the material RP/I and others that members were already familiar with.

I think I have the article I will find it and post it and file it in the archives .......
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Direct conversion of aldehydes, esters, and 1,2-oxides to alkanes with carbon skeleton preservation
E. E. Van Tamelen and J. A. Gladysz
J. Am. Chem. Soc. 1974, 96, 5290
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.......as for the March reference,

This article I wasn't familiar with, I will put it in the wanted references see if we can acquire it to post here...........java
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Reduction of N-acyl,N?-tosylhydrazines with diborane : A simple, convenient procedure for the conversion of the carboxylic to the methyl group

O.Attanasi, L. Caglioti, , F. Gasparrini and D. Misiti
Tetrahedon 1975, 31, 341

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Note: an interesting side note as to the works with Phenylalanine , ning over at WD has been coming out with some interesting conversions of the phenylalanine to the alkane amine and also the methylated alkane amine.......see

http://www.wetdreams.ws/forum/topic.asp?TOPIC_ID=3255

CherrieBaby · chouchou

loki · guinea pig

on one of the associated sites related to that site um i dunno what it's called something about hedonic something, they have collected heaps of studies about drugs... ah yess, bltc.org... and here is a synth they show for it (starting from phenylalanine)

one step, at least, is fairly easy to understand, first make the methyl ester (hey, isn't that what nutrasweet has in it incidentally) and then formylate and reduce to the methyl-amine. the conversion of the acid to the alkyl radical is done via halogenation and reduction. It is vaguely possible that would work with a zinc chloride reduction or even maybe red phosphorous/iodine. I think halogenation/reduction is likely to be the most accessible route. (edit: oops, the acid is reduced to the alcohol first) damn... well if a facile route to reducing the acid back to an alcohol can be found, that's gonna be a good intermediate step, because reducing the alcohol is something we all know how to do Wink

IndoleAmine · Dreamreader Deluxe

java · Consumer

Phenylalaninol to alkane via chlorination and reduction has been continued on this thread

Namely because it's a procedure discussed in the essential chemistry forum......java

java · Consumer

Here is an article recently posted in another thread , for which I thought this was the place to post it.as it comments on the article all ready posted here .................java
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Efficient Procedure for the Reduction of r-Amino Acids to Enantiomerically Pure
r-Methylamines
Dominick A. Quagliato,*,† Patrick M. Andrae, and
Edward M. Matelan
J. Org. Chem. 2000, 65, 5037-5042

Summary
We have demonstrated an efficient new method for the
reduction of amino acids into R-methylamines that does
not racemize the R carbon. This procedure should be
applicable for suitably protected amino acids and for the
reduction of carboxylic acids in a variety of systems.

Interesting points and methods fond on this citation..........