198019-15-7Relevant academic research and scientific papers
Synthesis of 2- and 3-trifluoromethylmorpholines: Useful building blocks for drug discovery
Shcherbatiuk, Andriy V.,Shyshlyk, Oleg S.,Yarmoliuk, Dmytro V.,Shishkin, Oleg V.,Shishkina, Svitlana V.,Starova, Viktoriia S.,Zaporozhets, Olga A.,Zozulya, Sergey,Moriev, Roman,Kravchuk, Olga,Manoilenko, Olga,Tolmachev, Andrey A.,Mykhailiuk, Pavel K.
, p. 3796 - 3804 (2013/07/05)
2- and 3-Trifluoromethylmorpholines were prepared in racemic and optically active forms. The synthesis commenced from the commercially available 2-trifluoromethyloxirane. The elaborated procedures were scalable, and the products were obtained in multigram quantities. The obtained compounds were comprehensively characterized by crystallographic analysis, fluorescence measurements, solubility, pKa, logD parameters, and clearance rate. The potential of the synthesized amines as the building blocks for drug discovery is thus demonstrated.
Intramolecular S(N)2 reaction at α-carbon of trifluoromethyl group: Preparation of optically active 2-trifluoromethylaziridine
Katagiri, Toshimasa,Ihara, Hideki,Takahashi, Mikihiro,Kashino, Setsuo,Furuhashi, Keizo,Uneyama, Kenji
, p. 2933 - 2937 (2007/10/03)
We have succeeded in intramolecular nucleophilic substitution of the hydroxyl group in (S)-1-(alkylamino)-3,3,3-trifluoro-2-propanol. The reaction provides an optically pure (R)-1-benzyl-2-trifluoromethylaziridine in good yield from optically pure (S)-3-(benzylamino)-1,1,1-trifluoro-2-propanol which was prepared from (S)-3,3,3-trifluoropropene oxide (75% ee).
