04-16-04 22:18
No 501112
I looked, but did not find.
In one version of tryptamine synthesis, oxalyl chloride is condensed with indole, then the stuff alkylates some amine to give this (I don't know what it's called)
Molecule: intermediate ("c1nc2ccccc2c1C(=O)C(=O)N(C)C")
Which is then reduced with LiAlH4, usually. Every reaction on beilstein does this. Maybee some bee has used the clemenson reduction also, I do not know.
What I would like to know is whether a Wolff-Kishner reaction would remove those carbonyls, or reaction conditions would destroy the tryptamine. (Pictet-Spengler, Lili?
Or something?)I guess if acidic conditions cause that, it would be a strike against the Clemenson. But Wolff-Kishner is basic. Any threads here on this matter already? UTFSE again?
Catching a buzz @ the Hive
(Heavyweight Chempion(eer))
04-16-04 22:26
No 501115
The carbonyl closest to the ring (the aromatic carbonyl) shouldn't be a problem to reduce with any of the regular methods for reducing them. I don't know what would happen with the amide though. But I suspect it would survive since they tend to be tough bastards. The amide can then be reduced to the amine with e.g. sodium triacetoxyborohydride (which can be found in TFSE).
The intermediate is a N,N-disubstituted indolyl-3-glyoxylamide
(Hive Bee)
04-16-04 22:31
No 501116
I don't know what would happen with the amide though. But I suspect it would survive since they tend to be tough bastards.
Survive the conditions for the Wolf-Kishner? Like >150°C, KOH and hydrazine in glycol? No way. This bastards are not that tough.
“The real drug-problem is that we need more and better drugs.” – J. Ott
(Heavyweight Chempion(eer))
04-16-04 22:51
No 501120
Bah! I'd take a Wolff-Kishner any day of the week.
On second thought, you might have point there. How about the Clemmensen then?
(Hive Bee)
04-17-04 13:11
No 501259
I guess there are possibilities for the amide to come out of the Clemmensen more or less intact, but this reduction is known to sometimes cause impredictable results with substrates that are more than just plain ketones (have other functions as well). Besides I don't even know if it works for beta-keto-amides. The indole group can also bee cause for many unpredictabilities (just think of the NaBH4 reduction of 3-acethyl-indoles). And then, what should be done with the amide group? Just don't say LiAlH4 please.
Edit: The best thing to try out would bee a NaBH4 reduction of both the amide and the keto group like in ../rhodium/clandestine/dmt/i
“The real drug-problem is that we need more and better drugs.” – J. Ott
(Heavyweight Chempion(eer))
04-17-04 16:41
No 501286
Nicodem, you obviously did not read the entire post I made above. Use STAB for the amide.
(Hive Bee)
04-17-04 17:20
No 501294
Sorry.
However, a two step reaction is not tempting at all.
What, do you think of a one step alternative, something cleaner than Clemmensen? Hey, I think your STAB should do just well for both keto groups.
“The real drug-problem is that we need more and better drugs.” – J. Ott
(acetaminophanatic)
04-28-04 05:00
No 503408
Searched beilstein a little more carefully, and I found two types of reactions.
In the first case, indole-CH2CH2COOMe + N2H4 --> indole-CH2CH2CONHNH2
In the second case, yohimbine (which contains the tryptamine core) is treated to the wolff-kishner.
I don't know if this is of use, but it is suggestive that tryptamines MIGHT survive.
I've been chased by both cops and robbers. So what does that make me?