solo
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zinc and water to decarboxolate phenylalanine to an alcohol
Prior to Gringard there was zinc and it was used widely to do many reductions halogenations and combined with chloride and HCl that is still true
today. I've been looking for info on reduction of the carboxylic acid of pheneylalanine and it s conversion to an alcohol.......any suggestions or has
anyone any references .......thanks
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solo
International Hazard
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Re: phenylalanine >>>>alcohol
?"R\uccess, so sodium borohydride will work with H2SO4 since it's a more selective carbonyl reducing agent, no need to worry about the amine group
since it won't be effected.
see http://www.rhodium.ws/pdf/borohydride-iodine.pdf
.............solo
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Polverone
Now celebrating 21 years of madness
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hmmm
Sodium borohydride and phenylalanine are both pretty expensive. Isn't this is a rather costly route to amphetamine? And it needs sodium borohydride,
which I would assume is at least informally watched.
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solo
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RE: cost and availability............
Well as a nutritional additive 1kg sells for $340 sodium borohydride sells for 500gr. for $100 , as you know sodium borohydride is used to make fuel
cells and as a medium to store hydrogen in the batteries........it may be watched but not prohibited from acquisition.
........................solo
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solo
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Ref: Phenylalanine Reduction to something useful.....
Here is another way to possibly reduce this amino acid to something useful.......
C6H5-CH2-CH(-NH2)-COOH-->C6H5-CH=C(-NH2)-COOH
........(Phenylalanine)
My first thought is to dehydrate the compound in a reflux of H2SO4 , which being acidic it will not disturb the NH2 and may just remove the H from the
#2C and establish a stable double bond between C1and C2 as opposed to C2and C3.
The interest underlying would be to catalytic hydrogenate the allyl compound with Pd and CH3CH2OH to the alcohol and even down to the alkane
.......solo
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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solo
International Hazard
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Ref: Phenylalanine Reduction to something useful.....
Now it's been documented the reduction of phenyalanine to the alcohol Phenylalaninol using NaBH4/I + H2SO4 and needing THF as a solvent. This
method doesn't employ either Iodine nor H2SO4.........solo
-------------------------------------------------------------------
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
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.
read more ....
Attachment: Transition Metal Compound Mediated Reduction of -Amino Acids to 1,2-Amino Alcohols with NaBH4 in Water (Turk J. Chem 19 (97kB)
This file has been downloaded 1250 times
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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Organikum
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I came to the believe that the only useful way of processing the l-phenylalanine of trade to something more useful is a hypochlorite degradation to
benzylcyanide and working with this, either by making PAA or P2P as well known.
l-phenylalanine has just the wrong stereochemistry and d or d/l-phenylalanine is expensive and hard to get, at least for me.
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