The Vespiary
The Hive => Novel Discourse => Topic started by: PEYOTE on October 07, 2001, 09:41:00 PM
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I've UTFSE and seen that there are some post talking 'bout ICE produced by urea and something else. I've mumbled this, from P1P alpha-halogenated and urea.
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000221311-file_ykrs.gif)
I'll look for refs for every single steps....
For now, what do you think about this? Have anyone any idea for the reduction in the last step?
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I've found some refs for ICE and a route like this:
On Beilstein (BRN 149933) there are 5 type of reactions; I've found that on Yakugaku Zasshi (a Japanese journal of pharmacological chemistry), (1948), 68, 70 it is possible make ICE from 1,2-dibromo-1-phenylpropane (from propenylbenzene!) and urea.
Other refs are:
on the same journal, (1978), 98(5), 611-617;
Heterocycles, (1997), 6(9-10), 1604-9
Berichte, (1931), 64, 1076-86 (in german!)
J. Med. Chem., (1963), 6, 266-72 (with CNBr, usual route)
On Chemical Abstract:
93:220636x --> Eur. J. Med. Chem. - Chem. Ther., (1980), 15(2), 111-17 (also this in german)
Unfortunately I cant achieve these refs and I dont know gernan, so I someone could please help me... ;)
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Here's the CA entry from the abovementioned article which supposedly would tell us how to go from 1-phenyl-1,2-dibromopropane to 4-MAR with urea, but unfortunately it seems like this short abstract is incomplete. But nevertheless, it still contained some interesting information about ephedrine-relaed chemistry.
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000221311-chem_abs_1054_1950.gif)