Author Topic: A Completely New Coca Analog  (Read 917 times)

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zorohydride

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A Completely New Coca Analog
« on: February 22, 2003, 05:25:00 PM »
Hello Chemists!
I have thought about this molecule for sooo long but dont have a lab anymore so I thought that I would toss it out to the lions for general discourse. Here is my synthesis! We start with n-Methyl-4-Piperidone and react with Dimethyl Carbonate and Sodium Methylate {or Sodamide in appropriate solvent} to get our intermediate, n-Methyl-3-Carbomethoxy-4-Piperidone. A facile reduction with NaBH4 in any alcoholic, or preferably hydro-alcoholic solvent (except methanol)to give us the 'exo alcohol' with subsequent workup and extraction with DCM should yield the ...3-Carbomethoxy-4-Piperidin-ol. So far, I haven't proposed anything to tricky. We now dry the DCM and react with Benzoic Anhydride to get the benzoyl ester in pretty high yield. Basify and extract with H2O from the DCM reaction waste components. Acidify the DCM to pH6, seperate, and dilute with Acetone to get an interesting molecule similar to coca cola without the ethylene bridge that would make up a tropane alkaloid. So bees and gees, what do yo think. I say we send Igor out to fetch us a normal brain!

roger2003

  • Guest
coca
« Reply #1 on: February 23, 2003, 02:52:00 PM »
The fist step in the coca-synthesis is usually the condensation of 2,5-dimethoxytetrahydrofurane (succindialdehyde), methylamine and the monopotassiumsalt of 3-oxoglutaric-acid-dimethylester (or the monoester via the anhydride of 3-oxoglutaric-acid)  to 2-carbomethoxytropinone.

If you change methylamine to another amine ( ethylamine etc.) or  succindialdehyde with substituted analogs in this condensation step or another ester (ethyl pp.) of 3-oxoglutaric-acid, you have a lot of active anlalogic compounds.

zorohydride

  • Guest
No! No! No! Please do not spew out Findlay's...
« Reply #2 on: February 23, 2003, 04:08:00 PM »
No! No! No! Please [1] do not spew out Findlay's JOC refernece to 2-Carbomethoxytropinone and [2] please DRAW THE MOLECULE i have proposed! I have performed Findlays' synthesis many years ago in a galaxy far away and it is as brilliant a synthetic startegy as it is laborious. I am not proposing a coca TROPANE dead on stereospecific knock-off but a Piperidine cousin; hence the name analog! Now, draw a picture of N-Methyl-Piperidine with a keto group in the '4' position[AKA n-Methyl-4-Piperidone, a readily available starting material] directly opposite from the methylamine group. My synthesis proposes that we put a carbomethoxy [methyl ester] next door to the keto group, then reduce the keto group in water [preferably with sodium borohydride stabilized solution] to preserve the 'exo' orientation of alcohol production [please see Findlay's paper for the justification], and then we form a benzoyl ester to that alcohol. What you will now have is a piperidine alkaloid analog. If you place an ethylene bridge across the 2 & 5 positions of the piperidine, you will have a tropane. Why go through all that trouble. I am betting that piperidine analog 'sans the ethylene bridge' should be very active. By the way newbie, I appreciate the way you went after this, but if you like Findlay, look up his little known synthesis that appeared the next year in JOC, he made a pseuopelletierine analog with readily available glutaraldehyde and got activity.


roger2003

  • Guest
Cocain = Tropane Alkaloid ; Maybe, you have...
« Reply #3 on: February 23, 2003, 07:33:00 PM »
Cocain = Tropane Alkaloid ; Maybe, you have another nomenklature for compounds and persons  :)

zorohydride

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(Post deleted by zorohydride)
« Reply #4 on: March 03, 2003, 12:27:00 AM »
(empty)

Rhodium

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References does wonders for your response
« Reply #5 on: March 03, 2003, 12:51:00 AM »
Us real scientists has seen too much of unfounded theories here at the Hive and elsewhere to not be especially amused by speculations not backed up by solid claims or references.