Synthesis of side-chain monofluorinated amphetamines
1980; Elsevier BV; Volume: 16; Issue: 3 Linguagem: Inglês
10.1016/s0022-1139(00)85218-5
ISSN1873-3328
AutoresRonald T. Coutts, A Benderly, Allan Mak,
Tópico(s)Chemical Synthesis and Analysis
ResumoR- and S-2-Amino-3-fluoro-1-phenylprupane were prepared in approximately 50% yields by the action of HF-pyridine on R- and S-2-benzylaziridine. (±)-2-Amino-3-fluoro-1-(4-chlorophenyl)propane was similarly prepared from (±)-2-(4-chlorobenzyl)aziridine. Structures of products were confirmed by n.m.r. and mass spectroscopy. In contrast, when 2-benzyl-N-tosylaziridine was reacted with HF in pyridine, the C2 atom of the aziridine ring was the site of fluorination and the N-tosylated derivative of 3-amino-2-fluoro-1-phenylpropane was obtained in excellent yield.
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