Author Topic: Phenylalanine to amphetamine or N-methylamphetamine (Read 4475 times)

Naf1 · « **Reply #40 on:** April 09, 2010, 10:30:02 PM »

@Enk, the paper below was OCRed. Please replace with your existing copy.

Chlorotrimethylsilane/Sodium Iodide/Zinc as a Simple and Convenient Reducing System; One-Pot Deoxygenation of Alcohols and Ethers
http://127.0.0.1/Naf1/Chlorotrimethylsilane,%20Sodium%20Iodide,%20Zinc%20as%20a%20Simple%20and%20Convenient%20Reducing%20System%3b%20One-Pot%20Deoxygenation%20of%20Alcohols%20and%20Ethers.pdf

Anyone wants any pdfs or djvus OCRed please pm me the relevant links.

Sedit · « **Reply #41 on:** April 09, 2010, 10:54:25 PM »

I posted a paper sometime ago over at TheZones that uses Diphenylchlorosilane I believe it was for the selective one pot deoxygenation of alcohols as a proposed method of converting PSE to AMP. The reaction seemed very viable but the expense was absurd. Something on the order of a 600$ would be needed just to reduce a couple grams of PSE. I honestly can not expect chlorotrimethylsilane to be much cheeper then its Diphenyl counterpart however if one could obtain it a world of possibilitys would open up.

Enkidu · « **Reply #42 on:** April 09, 2010, 11:08:07 PM »

Chlorotrimethylsilane costs $85/kg or $250/5 kg from Sigma-Aldrich. I am hoping that there's an otc prep somewhere...

Enkidu · « **Reply #43 on:** April 20, 2010, 10:20:43 AM »

Not too much luck with an OTC prep for chlorotrimethylsilane, but it's still an option if you want to buy it.

Here's a ref, useful in avoiding the need for tosyl chloride. Found by Nicodem.

ZrCl4 as an Efficient Catalyst for Selective Tosylation of Alcohols with p-Toluenesulfonic Acid
Biswanath Das and Vtukuri Saidi Reddy
Chemistry Letters Vol.33, No.11 pp.1428-29 (2004) DOI 10.1246/cl.2004.1428

Enkidu · « **Reply #44 on:** April 22, 2010, 08:48:32 AM »

acid --Li/amine-> aldehyde --Zn/HCl-> alkane.

Synthesis of aldehydes and secondary amines from carboxylic acids via imines
Angela O. Bedenbaugh, John H. Bedenbaugh, W. A. Bergin, James D. Adkins
J. Am. Chem. Volume 92, Issue 19 pp 5774–5775 (1970) DOI: 10.1021/ja00722a060

java · « **Reply #45 on:** April 24, 2010, 11:00:35 PM »

Quote from: Enkidu on April 20, 2010, 10:20:43 AM

Not too much luck with an OTC prep for chlorotrimethylsilane, but it's still an option if you want to buy it.

Here's a ref, useful in avoiding the need for tosyl chloride. Found by Nicodem.

ZrCl4 as an Efficient Catalyst for Selective Tosylation of Alcohols with p-Toluenesulfonic Acid
Biswanath Das and Vtukuri Saidi Reddy
Chemistry Letters Vol.33, No.11 pp.1428-29 (2004) DOI 10.1246/cl.2004.1428

...........i saw this over at SM and at the time had a question ......how does one remove the tosyled group from the once alcohol..... reflux wih KOH in MeOH ? This would be a good method for my phenylalaninol project......java

Enkidu · « **Reply #46 on:** April 26, 2010, 02:35:30 AM »

Probably.

Quantum Dude · « **Reply #47 on:** April 30, 2010, 02:33:46 PM »

The Bouveault-Blanc reduction is a good alternative to hydride reduction of esters to corresponding alcohol.

madprossor · « **Reply #48 on:** May 09, 2010, 12:52:00 AM »

hey dude, direct reduction by Diborane in THF is also an alternative. i think you still need to make esters before doing the Bouveault-Blanc.

also yeast would give 2-phenylethanol from phenyalanine by the method of Erlich but the solvent volumes are ridiculous. i say it will definitely work though.

JohnWestern, HI reduction of the phenylalainol would then give alpha-ethyl-phenethylamine as your final product...?

German · « **Reply #49 on:** May 09, 2010, 09:50:31 PM »

Making the ester by cooking in sulfuric acid for 3 hours and then reducing to phenylalainol with sodium borohydride was done several times by me. I just never took it further then that. But those first two steps are easy and high yield......

Leave out the personal info, please - Enkidu

madprossor · « **Reply #50 on:** May 14, 2010, 10:39:57 PM »

cool! i wonder then if indole-3-ethanol is similarly achieved from IAA with borohydride? (this is not yet documented in the literature.)

shroomedalice · « **Reply #51 on:** May 14, 2010, 11:26:38 PM »

you little ripper enkidu I knew that would work but for the life of me could not find a paper on it.

so its ether herring sperm and lithium to aldehyde then one wolff kishner too amphet nice one.

I think you will get cleavage of the amine group with a Clemmensen reduction

on further reading it seems that the yeild would be rather low.

having said that I have a couple of papers on WD about cathodic birch reductions that are used to reduce anisol with out hurting the

aromatic ring.

ill tag them down here seems the birch will reduce an acid.

shroomedalice · « **Reply #52 on:** May 15, 2010, 12:12:50 AM »

http://pubs.acs.org/doi/abs/10.1021/jo00205a003
http://pubs.acs.org/doi/abs/10.1021/jo00171a011

that should give you something to think about anyway.

java · « **Reply #53 on:** June 28, 2010, 04:31:07 PM »

.....as it happens sometimes amines have to be protected for valuable reductions of aminoalcohols with HI can happen......? clue......java

Warwick · « **Reply #54 on:** June 29, 2010, 07:48:43 PM »

Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp3?Csp) of Natural ?-Amino Acids and Alkynes

Quote

An interesting aldehyde- and ketone-induced intermolecular tandem decarboxylation-coupling (Csp3?Csp) catalyzed by copper with use of natural ?-amino acids as starting materials is developed under neutral conditions with the production of CO2 and H2O as the only byproducts. Various functionalized nitrogen-containing compounds were obtained by this method. In these processes, interesting regioselectivites of the alkylation were observed, which has been rationalized by the relative stability of proposed resonance structures based on computation methods.

Unsure if the if the article could be of an applicable nature to the topic. The mechanism would seem to be ideal on the surface given the resulting methylated amino. I'd have to see the actual article to go any farther.

EDIT: Fixed link, adding to request thread...
EDIT... I no longer have access to the reference forum it seems, anyone else that would request for me? thanks.

java · « **Reply #55 on:** July 29, 2010, 03:47:06 PM »

Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp3?Csp) of Natural ?-Amino Acids and Alkynes
Hai-Peng Bi†‡, Qingfeng Teng‡, Min Guan‡, Wen-Wen Chen†, Yong-Min Liang
J. Org. Chem.
2010, 75 (3), pp 783–788
DOI: 10.1021/jo902319h

java · « **Reply #56 on:** July 29, 2010, 03:48:58 PM »

Requested by shroomedalice....that should give you something to think about anyway.

Selective cathodic Birch reductions
Essie Kariv-Miller, Karl E. Swenson, Gaye K. Lehman, Romano Andruzzi
J. Org. Chem.
1985, 50 (5), pp 556–560
DOI: 10.1021/jo00205a003

-----------

Cathodic Birch reduction of methoxy aromatics and steroids in aqueous solution
Essie Kariv-Miller, Karl E. Swenson, Dvora Zemach
J. Org. Chem.
1983, 48 (23), pp 4210–4214
DOI: 10.1021/jo00171a011

java · « **Reply #57 on:** August 24, 2010, 04:26:57 PM »

this may be of interest......it's called d-1-phenyl-2 amino-3-iodopropane. Hydrochloride when d-phenylalaninol is iodated....java

Uploaded with ImageShack.us

jon · « **Reply #58 on:** August 24, 2010, 08:03:10 PM »

that upload did'nt work

shroomedalice · « **Reply #59 on:** August 25, 2010, 04:44:07 AM »

hey cool pic java thats the product after reduction and iodation of a henry reaction with nitroethanol and benzaldehyde as well. get this right and you have all the substitutions as well.

Author Topic: Phenylalanine to amphetamine or N-methylamphetamine (Read 4475 times)

Naf1

Re: Phenylalanine to amphetamine or N-methylamphetamine

Sedit

Re: Phenylalanine to amphetamine or N-methylamphetamine

Enkidu

Re: Phenylalanine to amphetamine or N-methylamphetamine

Enkidu

Re: Phenylalanine to amphetamine or N-methylamphetamine

Enkidu

Re: Phenylalanine to amphetamine or N-methylamphetamine

java

Re: Phenylalanine to amphetamine or N-methylamphetamine

Enkidu

Re: Phenylalanine to amphetamine or N-methylamphetamine

Quantum Dude

Re: Phenylalanine to amphetamine or N-methylamphetamine

madprossor

Re: Phenylalanine to amphetamine or N-methylamphetamine

German

Re: Phenylalanine to amphetamine or N-methylamphetamine

madprossor

Re: Phenylalanine to amphetamine or N-methylamphetamine

shroomedalice

Re: Phenylalanine to amphetamine or N-methylamphetamine

shroomedalice

Re: Phenylalanine to amphetamine or N-methylamphetamine

java

Re: Phenylalanine to amphetamine or N-methylamphetamine

Warwick

Re: Phenylalanine to amphetamine or N-methylamphetamine

java

Re: Phenylalanine to amphetamine or N-methylamphetamine

java

Re: Phenylalanine to amphetamine or N-methylamphetamine

java

Re: Phenylalanine to amphetamine or N-methylamphetamine

jon

Re: Phenylalanine to amphetamine or N-methylamphetamine

shroomedalice

Re: Phenylalanine to amphetamine or N-methylamphetamine