M. D’hooghe, Alex Waterinckx, Tim Vanlangendonck
Mar 6, 2006
Citations
0
Influential Citations
20
Citations
Journal
Tetrahedron
Abstract
Abstract 1-Arylmethyl-2-(bromomethyl)azirdines were converted into the corresponding 2-(aryloxymethyl)aziridines upon treatment with the appropriate potassium phenoxides in DMF/acetone in excellent yields, followed by regioselective ring opening towards N , N -di(arylmethyl)- N -(2-bromo-3-aryloxypropyl)amines using benzyl bromide in acetonitrile. Treatment of the latter β-bromoamines with sodium methoxide afforded the desired 2-amino-1-aryloxy-3-methoxypropanes as the major compounds (49–58%) besides the isomeric 3-amino-1-aryloxy-2-methoxypropanes in minor quantities (9–15%).