Rhodium
(Chief Bee) 09-26-02 07:17 No 360757 |
New tryptamine synthesis? | Bookmark | ||||||
Couldn't (S)-2-tert-butoxycarbonylaminopropyl methanesulfonate used for the alkylation somehow be used for 3-alkylation to form alpha-methyltryptamines? Or could it be applied to amphetamines, by some kind of aryl halide/mesylate coupling? |
||||||||
Barium (Hive Bee) 09-26-02 07:31 No 360763 |
I have no clue if it could be used. | Bookmark | ||||||
I have no clue if it could be used. But I´m pretty sure Os or Lillienthal have ideas about it. Catalytic hydrogenation freak |
||||||||
pHarmacist (Hive Bee) 10-05-02 19:04 No 364924 |
To Rhodium | Bookmark | ||||||
I think that this would be fully possible, and of course much easier from indolum.... A little reminder of our conversation of my Wolff/Kishner thread in Stimulants :) [pH]armacist - Never, never ever shall you underestimate the power of retrosynthesis... |
||||||||
Rhodium (Chief Bee) 10-05-02 21:38 No 364950 |
Oh - do you have any references for the first ... | Bookmark | ||||||
Oh - do you have any references for the first reaction? I have never seen anything being alkylated by the sulfur equivalent of an orthoester before... |
||||||||
pHarmacist (Hive Bee) 10-05-02 21:53 No 364955 |
On monday | Bookmark | ||||||
My professor is constantly talking about that particular reaction, I have no reference but I can ask the old geezer about his refs on monday, although I don't like arguing with him when it comes to chemistry, what he saiz goez.. [pH]armacist - Never underestimate the power of retrosynthesis. Svenskar suger på fotboll! |
||||||||
pHarmacist (Hive Bee) 10-05-02 22:06 No 364957 |
When I look at it it seems logical, CH3S goes, ... | Bookmark | ||||||
When I look at it it seems logical, CH3S goes, carbocation is formed, attack from the 3-carbon of indole, works fine... [pH]armacist - Never underestimate the power of retrosynthesis. Svenskar suger på fotboll! |
||||||||
hest (Hive Adickt) 10-06-02 03:09 No 365004 |
Beilstain | Bookmark | ||||||
A beilstein search on the thiothing(and related structure) gave no hits, that might bee a hint ?. |
||||||||
pHarmacist (Hive Bee) 10-06-02 03:21 No 365006 |
OrgSyn | Bookmark | ||||||
This could also be a hint, exacly the reaction I was talking about: 3-ALKYLATED AND 3-ACYLATED INDOLES FROM A COMMON PRECURSOR: 3-BENZYLINDOLE AND 3-BENZOYLINDOLE Submitted by: P. Stütz and P. A. Stadler Published in Annual Volume 56, page 8; Collective Volume 6, page 109 http://www.orgsyn.org [pH]armacist - Never underestimate the power of retrosynthesis. Svenskar suger på fotboll! |
||||||||
dmitri (Stranger) 10-06-02 10:44 No 365075 |
The mesylate ester is being used as an ... | Bookmark | ||||||
The mesylate ester is being used as an N-alkylating agent. This reaction follows a classic SN2 mechanism, and I have a hard time imagining that the 3-position is going to be an option. I'm kind of surprised that they're using NaCNBH3 to remove the protecting group; TFA or even HCl in EtOAc will do this nicely for a lot less money. |
||||||||
GC_MS (Hive Bee) 10-06-02 14:39 No 365156 |
Looks... | Bookmark | ||||||
Looks like some sort of Friedel-Crafts with BF3 as the Lewis acid. The dithiane can be converted to -CH2- with Raney Ni (or hydrazine), as said by pHarmacist.
|
||||||||
GC_MS (Hive Bee) 10-06-02 15:15 No 365173 |
aldehydes... | Bookmark | ||||||
It might be interesting to note that the method might also be applicable for the synthesis of aldehydes... If the following dithiane is used:
WOMAN.ZIP: Great Shareware, but be careful of viruses... |
||||||||