Synthesis of Enantiomerically Pure Threo 1-Alkyl-2-benzyloxy-propylamines

Article abstract of DOI:10.1016/0957-4166(95)00433-5

Pure (1S,2S)-1-Butyl- and (1S,2S)-1-isobutyl-2-benzyloxy-propylamine have been synthesized in 5 steps and 62% overall yield from (S)-ethyl lactate. It was found that BuLi and i-BuMgBr add readily and diastereoselectivety (d.e.> 96 %) to α-benzyloxypropionaldehyde dimethylhydrazone and that hydrogenolysis proceeds in high yield and without epimerization.