Hive Tryptamine Chemistry

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	Tryptamine Chemistry

All 5 posts Subject: Suggested 2 step reaction to AMT Please login to post Down

Rhenium
(Member)
04-04-00 15:11
No 126930
      Suggested 2 step reaction to AMT
(Rated as: good read)

Hello everyone, it's been a long while since I walked these hallowed halls, but I had an idea kind of spring itself upon me as I sat in the lab musing over a few synthetic papers...
http://rhodium.lycaeum.org/chemistry/it-290.html

As everyone knows, the above link is to the synthesis of AMT located on Rhodium's page. Being more interested in synthetic chemistry than it's personal use, I wondered about a synthesis starting from that ubiquitous material Tryptophan.

Ok, here's the plan...

1) Reduction of Tryptophan or it's ester by the usual routes i.e. LiAlH4 or BH3/THF.

2) Elimination of that pesky alcohol group to it's corresponding methyl which takes us to our finished compound.

Ok, the first part is relatively simple, but what about the second? You can't reduce the group using standard methods, so how about these two papers which have definitely graced the Hive before...

1) Olah, G.A. et. al., J. Org. Chem., 44(8), 1979, pp 1247.

2) Sakai, T., et. al., Tet. Let., 28(33), 1987, pp 3817.

Both of these papers are different spins on Me3SiCl and NaI. The first turns the alcohol into a Iodide, and the second eliminates it all together. Both sets of reaction proceed at room temperature in good to excellant yield.
Three question therefore arise, 1) Can this chemistry be applied to indole containing system for the elimination of the slcohol, 2) what if any side-reactions may occur, and 3) if the iodide is isolated, what subsequent reaction can be used to eliminate that?

I leave these questions in your capable hands for further pondering...

Yours, as always...

Rhenium

rev drone
(Member)
04-04-00 18:08
No 126931
      Suggested 2 step reaction to AMT

Say, if memory serves, I think NaBH4/I2 as a reducing system is effective at facilitating the reduction of amino acids cheaply and effectively. I remember posting

------------------
-the good reverend drone

Ipsa scientia potestas est

Rhodium
(Chief Bee)
09-17-04 21:37
No 531846
User Picture       Tryptophan ester -> α-Methyltryptamine
(Rated as: excellent)

Synthesis of S(+)- and R(-)-3-(2-Aminopropyl)indole from Ethyl-D- and L-Tryptophanate
David B. Repke and Wilfred J. Ferguson
J. Heterocyclic Chem., 13, 775 (1976) (https://www.rhodium.ws/pdf/ethyl.tryptophanate2amt.pdf)

Abstract
A stereospecific requirement for hallucinogenesis applies to certain molecules containing an asymmetric center. Thus, only the R-isomers of substituted phenylisopropylamines and lysergic acid diethylamide are psychotomimetic. The enantiomers of a minor hallucinogen, S(+)- and R(-)-3-(2-aminopropyl)indole (α-methyltryptamine) (6a and 6b) were synthesized via a 5-step manipulation from D- and L-tryptophan ethyl ester hydrochloride, respectively. Optical purity of these two isomers was determined by pmr spectroscopy of their complexes with a europium chiral shift reagent using the indole C₂ H signal.

^{The Hive - Clandestine Chemists Without Borders}

Sedrick
09-19-04 17:50
      I was having a conversation with some chemists
(Rated as: insignificant)

Fastandbulbous
(Hive Bee)
09-21-04 01:54
No 532414
User Picture       Applying to other amino acids

Surely that means that, by the above method, that phenylalanine can be converted into amphetamine, tyrosine to 4-hydroxyamphetamine and best of all DOPA to 3,4-dihydroxyamphetamine (then methylenation to MDA), and as phenolic OH groups don't undergo substitution reactions in the same way that aliphatic OH groups do, mean that they will be stable to reagents that convert the OH from reduction of the carboxylic acid to the intermediate iodo compound, or am I overlooking something simple (my area is pharmacology, with only a bit of org chem synth proceedures)?

That is right, the Mascara Snake: Fast and bulbous

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	All 5 posts		Subject: Suggested 2 step reaction to AMT		Please login to post		Down


		Rhenium (Member) 04-04-00 15:11 No 126930				Suggested 2 step reaction to AMT (Rated as: good read)
						Hello everyone, it's been a long while since I walked these hallowed halls, but I had an idea kind of spring itself upon me as I sat in the lab musing over a few synthetic papers... http://rhodium.lycaeum.org/chemistry/it-290.html As everyone knows, the above link is to the synthesis of AMT located on Rhodium's page. Being more interested in synthetic chemistry than it's personal use, I wondered about a synthesis starting from that ubiquitous material Tryptophan. Ok, here's the plan... 1) Reduction of Tryptophan or it's ester by the usual routes i.e. LiAlH4 or BH3/THF. 2) Elimination of that pesky alcohol group to it's corresponding methyl which takes us to our finished compound. Ok, the first part is relatively simple, but what about the second? You can't reduce the group using standard methods, so how about these two papers which have definitely graced the Hive before... 1) Olah, G.A. et. al., J. Org. Chem., 44(8), 1979, pp 1247. 2) Sakai, T., et. al., Tet. Let., 28(33), 1987, pp 3817. Both of these papers are different spins on Me3SiCl and NaI. The first turns the alcohol into a Iodide, and the second eliminates it all together. Both sets of reaction proceed at room temperature in good to excellant yield. Three question therefore arise, 1) Can this chemistry be applied to indole containing system for the elimination of the slcohol, 2) what if any side-reactions may occur, and 3) if the iodide is isolated, what subsequent reaction can be used to eliminate that? I leave these questions in your capable hands for further pondering... Yours, as always... Rhenium



		rev drone (Member) 04-04-00 18:08 No 126931				Suggested 2 step reaction to AMT
						Say, if memory serves, I think NaBH4/I2 as a reducing system is effective at facilitating the reduction of amino acids cheaply and effectively. I remember posting ------------------ -the good reverend drone Ipsa scientia potestas est



		Rhodium (Chief Bee) 09-17-04 21:37 No 531846				Tryptophan ester -> α-Methyltryptamine (Rated as: excellent)
						Synthesis of S(+)- and R(-)-3-(2-Aminopropyl)indole from Ethyl-D- and L-Tryptophanate David B. Repke and Wilfred J. Ferguson J. Heterocyclic Chem., 13, 775 (1976) (https://www.rhodium.ws/pdf/ethyl.tryptophanate2amt.pdf) Abstract A stereospecific requirement for hallucinogenesis applies to certain molecules containing an asymmetric center. Thus, only the R-isomers of substituted phenylisopropylamines and lysergic acid diethylamide are psychotomimetic. The enantiomers of a minor hallucinogen, S(+)- and R(-)-3-(2-aminopropyl)indole (α-methyltryptamine) (6a and 6b) were synthesized via a 5-step manipulation from D- and L-tryptophan ethyl ester hydrochloride, respectively. Optical purity of these two isomers was determined by pmr spectroscopy of their complexes with a europium chiral shift reagent using the indole C₂ H signal. ^{The Hive - Clandestine Chemists Without Borders}



		Sedrick 09-19-04 17:50				I was having a conversation with some chemists (Rated as: insignificant)



		Fastandbulbous (Hive Bee) 09-21-04 01:54 No 532414				Applying to other amino acids
						Surely that means that, by the above method, that phenylalanine can be converted into amphetamine, tyrosine to 4-hydroxyamphetamine and best of all DOPA to 3,4-dihydroxyamphetamine (then methylenation to MDA), and as phenolic OH groups don't undergo substitution reactions in the same way that aliphatic OH groups do, mean that they will be stable to reagents that convert the OH from reduction of the carboxylic acid to the intermediate iodo compound, or am I overlooking something simple (my area is pharmacology, with only a bit of org chem synth proceedures)? That is right, the Mascara Snake: Fast and bulbous

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