A New Green Method To Synthesize Vicinal Amino Alcohols

The vicinal amino alcohol moiety is a common structure component in a vastgroup of naturally occurring and synthetic molecules. The presence of this moiety andthe relative stereochemistry are generally important for the biological activity ofmolecules containing a vicinal amino alcohol. By now, there are a large number ofsynthetic routes to these molecules.This paper reports a new green ring opening reactions of aziridines with H₂O. Inthis new reaction, H₂O is nuclephile and solvent. The stirred mixture of N-tosylaziridine and water are heated to reflux. The reaction was completed in 8hr, and yieldsare from 62～93%. Under this reaction condition, seven vicinal amino alcohols, 2-hydroxy-2-phenyl-N-tosylamino ethane, 2-hydroxy-2-methyl-2-phenyl-N-tosylaminoethane,2-(4-chloridephenyl)-2-hydroxy-N-tosylaminoethane,2-(4-methylphenyl)-2-hydroxy-N-tosylamino ethane, 2-hydroxy-N-tosylamino cyclohexane, 2-hydroxy-N-tosylamino cycloheptane, 2-hydroxy-2-methyl-3-(N-tosylamino)-butane aresynthesized. All of the compounds have been determined by IR, ¹H NMR.This method is high-yielding, clean for ring opening of N-tosyl aziridines tovicinal amino alcohols, especially for small molecules. Further research is underwayon the detailed mechanism and other similar ring opening reaction in this laboratory.