10-07-02 07:43
No 365492
This is a result of my wild imagination rather than something serious, but could it work?
[pH]armacist - Never underestimate the power of retrosynthesis. Svenskar suger på fotboll!
(Hive Bee)
10-07-02 08:23
No 365504
The Stork enamine alkylation is a good idea, however I don't see how you can easily go from the ketone to the indole ring. Probably you need to reduce it first and then subject the alcohol to a beta-elimination.
The synthesis is a bit elaborate, but I don't see why the hell it shouldn't be possible. It looks OK, mechanistically speaking.
Glad to see you like retrosynthesis (it rules). Now, the following step would be: look up the reactions in the chemical literature to obtain lab procedures. If the yield are OK, your synthetic scheme would be great.
Keep up the good work
.
(Moderator)
10-07-02 13:48
No 365597
Nice idea. The last reaction can be accomplished with LiAlH4. But there might be a few problems:
- The first compound is not a ketone, it's an amide (or better: an anilide), so the first reaction might not work as expected.
- The second compound is not an enamine and will probably not react like one, it's an amino substituted aromatic ring similar to aniline.
- The product of the alkylation reaction will probably aromatize immediately, leaving you with a 2-pyrrolidyl-tryptamine.
(Hive Bee)
10-07-02 14:19
No 365609
The synthesis is a bit elaborate, but I don't see why the hell it shouldn't be possible. It looks OK, mechanistically speaking.
Damned, I 'm a bit ashamed here ... I completely overlooked the amide (stupid me ...). Yup, amides definitely don't react like ketones (resonance) ... so it won't work ...
(Hive Bee)
10-07-02 15:08
No 365629
Lilienthal: Of course, i didn't give it much thought, not at much all, it seemed ok then, but of course indolic nitrogen has a free e-par ... something I often miss when it comes to indolum :).. well I guess I'll have to dust myself off and try agin.. my bad thank you for remarks guys.. :(
[pH]armacist - Never underestimate the power of retrosynthesis. Svenskar suger på fotboll!