Best route to 5meo-Dipt is?

[Hierophant]

I posted to this forum before with this question (before the new board), and did not receive a satisfactory reply before the switchover. Is Shulgin's synthesis the best route to 5meo-Dipt (in terms of chemical availability and yield)? If not, then what would be a better route? The starting material is 5meo-T. Any ideas?

[Rhodium]

Another good way is to use the method for DIPT (#4 in Tihkal), but using 5-methoxyindole instead of regular indole in the process. The procedure wouldn't be much different.

http://rhodium.lycaeum.org

[kokopelli]

how about using 5-meo-Tryptamine (made from Melatonin),
sodium cyanoborohydride and isopropylbromide in a solution of methanol ?

koko

[psyloxy]

wouldn't that be acetone instead of iPrBr ?

Rhodium has a nice text in his archive that details exactly this kind of rxn.

--psyloxy--

[CHEM_GUY]

They will calll you and try to see if you are a legitamate researcher.  Only deleivered to business adresses as well.

This post is for informational purposes only an is not intended to facilitate illegal activity.

[Hierophant]

Would buy, except that I find it rather expensive (compared to preparing it from scratch). With Shulgin's method #37, it works out to about $400 for 12-14g (with enough chemicals left over to do it again, after puchasing more 5-Meo-Tryptamine. So so far this is the best method? I would like to avoid the high-boiling solvents of #37 (hexane and sulfolane), and I dislike working with LAH al la #4. Any ideas people?

[psyloxy]

Buy 5-MeO-Tryptophol, then it's only 2 steps [1:PBr3 or PI3][2:diPrNH] to foxy.

--psyloxy--

[Evil_Nefarious]

Re #37, what other solvents can be used?

Re 5-MeO-Tryptophol & 5-Meo-Tryptamine, just how watched are they?

[Evil_Nefarious]

I haven't checked exhaustively, barely even at all yet.  I would take that task on with a much happier air if you would expound upon your two step process above.

Mr. N

[psyloxy]

Phaidon: I checked chemfinder and some companys have it. There's also 7-OH and 6-MeO tryptophols and such... But not 4-OH-trytophol, sadly. Don't know what prices would be like but I think it is worth it since the 5-MeO's are that much more potent.

--psyloxy--

[psyloxy]

Evil:

http://rhodium.lycaeum.org/chemistry/tryptophol.txt

--psyloxy--

[Brivator]

Hi boys

With regard to the 1969 tryptaphol to tryptamine reaction:  isn't it a bit old-fashioned?  What about Mr. Mitsunobu?

With regard to Rhodium's comment that other forms of Ni can be substituted:  I recall from my pre-stripper days trying just such a reaction using Ra-Ni.  I'm pretty sure I got the reference for this from Larock.

With regard to converting to the bromide and then displacing with a secondary amine:  the second step might require a sealed tube (again, vague recollections from Larock).

When I get the shakes, I wiggle.