Efaroxan on:
[Wikipedia]
[Google]
[Amazon]
Efaroxan is an α2-adrenergic receptor antagonist and antagonist of the imidazoline receptor.
The Darzens reaction between 2-fluorobenzaldehyde 7848-46-1(1) and Ethyl 2-bromobutyrate 33-68-6(2) gives ethyl 2-ethyl-3-(2-fluorophenyl)oxirane-2-carboxylate
CID:100942311
(3). A catalytic hydrogenation over Pd/C would give ethyl 2- 2-fluorophenyl)methyl2-hydroxybutanoate
CID:77591056
(4).
CID:53869347
(5). Treatment with 2 molar equivalents of
Synthesis
The Darzens reaction between 2-fluorobenzaldehyde 7848-46-1(1) and Ethyl 2-bromobutyrate 33-68-6(2) gives ethyl 2-ethyl-3-(2-fluorophenyl)oxirane-2-carboxylateCID:100942311
(3). A catalytic hydrogenation over Pd/C would give ethyl 2- 2-fluorophenyl)methyl2-hydroxybutanoate
CID:77591056
(4).
Saponification
Saponification is a process of converting esters into soaps and alcohols by the action of aqueous alkali (for example, aqueous sodium hydroxide solutions). Soaps are salts of fatty acids, which in turn are carboxylic acids with long carbon chains ...
of the ester then gives 2- 2-Fluorophenyl)methyl2-hydroxybutanoic acidCID:53869347
(5). Treatment with 2 molar equivalents of
sodium hydride
Sodium hydride is the chemical compound with the empirical formula Na H. This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis. NaH is a saline (salt-like) hydride, composed of Na+ and H− ions, in ...
apparently gives 2-Ethyl-2,3-dihydrobenzofuran-2-carboxylic acid 11080-50-3
Eleven or 11 may refer to:
*11 (number), the natural number following 10 and preceding 12
* one of the years 11 BC, AD 11, 1911, 2011, or any year ending in 11
Literature
* ''Eleven'' (novel), a 2006 novel by British author David Llewellyn
*''El ...
(6). Treatment of the carboxylic acid with thionyl chloride
Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately per year bein ...
then gives the acid chloride and subsequent treatment of this with ethylenediamine
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately ...
in the presence of trimethylaluminium completed the synthesis of ' (8).
See also
* Fluparoxan *Idazoxan
Idazoxan (INN) is a drug which is used in scientific research. It acts as both a selective α2 adrenergic receptor antagonist, and an antagonist for the imidazoline receptor. Idazoxan has been under investigation as an antidepressant, but it d ...
References
External links
* Benzofurans Imidazolines Alpha-2 blockers {{drug-stub