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Communication | Special issue | Vol 54, No. 2, 2001, pp.589-592
Published online, 1st January, 1970
DOI: 10.3987/COM-00-S(I)80
Synthesis of α-(Trifluoromethyl)pyrrolidines by Cyclization of N-Tosyl-α-(trifluoromethyl)homoallylamine Derivatives

Itsumaro Kumadaki,* Shuichi Jonoshita, Kazuyuki Sato, Masaaki Omote, and Akira Ando

*Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan


Treatment of N-tosyl-α-(trifluoromethyl)homoallylamines (4), obtained by the ene type reaction of N-(2,2,2-trifluoro-1-ethoxyethyl)tosylamide (3), with a protic acid afforded N-tosyl-α-(trifluoromethyl)pyrrolidine derivatives (5 and 6). For example, 4-phenyl-N-tosyl-1-(trifluoromethyl)-3-butenylamine (4a) gave cis- and trans-2-phenyl-N-tosyl-5-(trifluoromethyl)pyrrolidines (5a and 6a). Interestingly, 6a was a major product in a moderate reaction condition, while 5a was a major product in more drastic conditions. The mechanism of these reactions is speculated. Treatment of 4a with iodine in the presence of sodium hydrogencarbonate brought about iodocyclization to give 3-iodo-2- phenyl-5-(trifluoromethyl)-N-tosylpyrrolidines (7 and 8).