J. Med. Chem. 37(19), 3029 (1994) (https://www.thevespiary.org/rhodium/Rhodium/pdf/reductive.tryptamination-2.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/reductive.tryptamination-2.pdf)Post 285474 (https://www.thevespiary.org/talk/index.php?topic=12713.msg28547400#msg28547400)
(Rhodium: "Tryptamine -> DMT w/ formaldehyde/NaBH3CN", Tryptamine Chemistry) were they also use sodiummethoxide in the synthese.Post 243844 (https://www.thevespiary.org/talk/index.php?topic=12768.msg24384400#msg24384400)
(Rhodium: "Tryptamine reductive alkylation with NaBH(OAc)3", Tryptamine Chemistry)https://www.the-hive.ws/forum/favorites.pl?Cat (https://www.the-hive.ws/forum/favorites.pl?Cat)
= (accessible by clicking "Show bookmarks" in your private area) so that you easily can go back to certain posts you want to read again without having to UTFSE for them every single time.Is the Cyanoborohydride required for this reduction or could NaBH4 be substituted? If it is a yields question I can live/ that
No, cyanoborohydride is not required, plain sodium borohydride can bee used, too.
A quick search with TFSE will tell you this ;)
The search string is almost in your post, perhaps you have to try an abbreviation but the hit will lead you to the right post.
Hint: The post you are looking for is quite new........
Post 431982 (https://www.thevespiary.org/talk/index.php?topic=12949.msg43198200#msg43198200)
(Lego: "Article on DMT derivate synths", Tryptamine Chemistry)but when i read that synth i can't see HOW that sulfonylmethyl group got in there in the first place, since none of the reagents listed carry a sulfur atom..? So this is where I go "What am I not seeing here???!!!"
Check Scheme 2 of the article. They use a 4-sulfonyl derivate of aniline. So the sulfur is in the molecule since the beginning of the synthesis.
The procedure for DMT would go like this:
A solution of 35% formaldehyde (35 mL, 416 mmol) in MeOH (35 mL) and a solution of NaBH4 (5 g, 132 mmol) in H2O (70 mL) were added dropwise, simultaneously, at 15°C to a well-stirred solution of tryptamine (4.166 g, 26 mmol) in MeOH (150 mL). The mixture was stirred at 15°C for 0.5 h, 2N aqueous HCl was cautiously added to bring the pH to 3, and the resulting mixture was stirred for 10 min. Then, the pH was adjusted to 6.5-7 with saturated aqueous NaHCO3, MeOH was evaporated, and H2O (50 mL) was added. The mixture was washed with EtOAc (2x150 mL), basified with K2CO3, and extracted with EtOAc (2x130 mL). The organic extracts were dried, filtered, and concentrated to give DMT.
All italic words are modifications of the original procedure.
The modification of the original procedure is quite simple, calculate the molar weight of tryptamine (either by hand or Merck Index or with a computer programm) multiply it with the molar amount and you get the weight of tryptamine you have to use. That's all, now try it yourself..........
Yields should be similiar to the original procedure (88%, about 4.3 g) but expect rather 2-3 g than 4 g if you do it the first time.
Good luck! 8)
Tetrahedron 57(6), 1041-1048 (2001) (https://www.thevespiary.org/rhodium/Rhodium/pdf/tryptamine.nabh4.methylation.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/tryptamine.nabh4.methylation.pdf), references the sodium borohydride reductive methylation of tryptamines fromPatent ES2084560 (http://l2.espacenet.com/dips/viewer?PN=ES2084560&CY=gb&LG=en&DB=EPD)
, where the procedure is largely the same.Post 436291 (https://www.thevespiary.org/talk/index.php?topic=13164.msg43629100#msg43629100)
(Lego: "What am I not seeing here?", Tryptamine Chemistry)Post 436291 (https://www.thevespiary.org/talk/index.php?topic=13164.msg43629100#msg43629100)
(Lego: "What am I not seeing here?", Tryptamine Chemistry) :P