for the synth outlined at Post 458401 (http://[url=https://www.thevespiary.org/talk/index.php?topic=9020.msg45840100#msg45840100)
(HumbleBee: "Norephedrine from benzaldehyde", Methods Discourse)=1&vc=1]
can a different tertiary amine be used in place of triethylamine ?
or would the old art with alkalimetal catalyst be easier ?
Yes - alkalihydroxides will do the job. They will however give a lower overall yield and a lower yield of the desired norephedrine stereoisomer. So depending on the intended use of your product, you should consider the following. If you simply want to reduce it to plain amphetamine, the alkalihydroxide "condensation" is fine. Also, if you have the balls(stupid enough?) to use cyanogen bromide, it's also a fine intermediate for 4-mar.
However, if you want to run the non-toxic cyanate route for trans-4-mar, you really should go for the trialkylamine route. Most lower trialkylamines will work as a catalyst, with the correst stereoisomer as the major product. From emperical knowledge I know that tributylamine will work quite well. The exact yield of the outcome using this as a catalyst, has not been measured.
Read this (https://www.thevespiary.org/rhodium/Rhodium/chemistry/para-fluoro-4-mar.html)
(https://www.thevespiary.org/rhodium/Rhodium/chemistry/para-fluoro-4-mar.html) for an example of the trialkylamine reaction.
Regards
Bandil
High Bandil!
I think this may be worth a try:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/nitro2amine.cth.pd-af.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/nitro2amine.cth.pd-af.html)
swil would give it a go this hour, if there would be any nitroethane left :( But this is going to change with time!
Would be gerat if you could try it on a small scale!
best wishes,
xicori