(S)-1-ARYLOKSY-2-PROPANOLDERIVATER FOR FREMSTILLING AV TERAPEUTISK AKTIVE (S)-1-ARYLOKSY-3-AMINO-2-PROPANOLDERIVATER

摘要

1458392 Optically active 1-aryloxy-2,3- epoxypropane derivatives IMPERIAL CHEMICAL INDUSTRIES Ltd 28 Oct 1974 [9 Nov 1973] 52077/73 Heading C2C The invention comprises an optically active epoxide having the (S)-absolute configuration and having the formula where RSP1/SP is an aryl radical which does not contain a nitrogen atom as part of the aromatic nucleus, and which may bear one or more substituents. RSP1/SP may for example be phenyl, a polycyclic aromatic radical wherein the ring to which the side chain is attached is a benzene ring, or a monocyclic heterocyclic radical; a wide variety of possible substituents for these rings is listed. The optically active epoxide may be made by treating with a base an optically active compound having the (R) configuration of the formula where Z is a displaceable radical, for example a halogen atom or an alkanesulphonyloxy or arenesulphonyloxy radical; the base may be an alcoholic or aqueous alcoholic solution of an alkali metal hydroxide. The preparations of a number of optically active compounds of formula are described. By reacting the epoxide of the invention with an amine RSP4/SPNH 2 , where RSP4/SP is an alkyl, hydroxyalkyl or cycloalkyl radical, an alkanolamine RSP1/SPOCH 2 .CHOH.CH 2 NHRSP4/SP having the (S)-absolute configuration is obtained; such alkanolamines have #-adrenergic blocking activity.