Aminoalcohols V [1]: A method for the synthesis of enantiomerically pure ring-chlorinated epinephrines and norepinephrines

The synthesis of enantiomerically pure 5- and 6-chloroepinephrine hydrochlo ride, resp., as well as 6-chloronorepinephrine hydrochloride is described s tarting from ring chlorinated O-benzylated dihydroxybenzaldehyde cyanohydri ns, which are O-protected using an enantiomerically pure acetal-type protec ting group (MBE). After lithium aluminum hydride reduction, followed - if n ecessary - by N-protection and methylation, removal of the chiral auxiliar and deprotection by hydrogenation furnished the target compounds with enant iomeric purities above 96% ee in high chemical yield, if well defined react ion conditions during the hydrogenation process were closely observed.