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Communication | Regular issue | Vol 14, No. 6, 1980, pp.775-778
Published online, 1st January, 1970
DOI: 10.3987/R-1980-06-0775
The Stereoselective Reduction of α-Aminopropiophenone Derivatives with Sodium Borohydride

Tetsuji Kametani,* Kazuo Kigasawa, Mineharu Hiiragi, Nagatoshi Wagatsuma, Toshitaka Kohagizawa, and Hitoshi Inoue

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


The ratio of erythro and threo products from the sodium borohydride reduction of the hydrochlorides, and other acid salts, of α-aminopropiophenone derivatives was determined. It was found that this procedure resulted in stereoselective formation of erythro-2-amino-1-phenylpropanols in contrast to sodium borohydride reduction of the corresponding free bases. The method was successfully applied to the synthesis of dl-erythro-2-(4-benzylpiperidino)-1-(4-hydroxyphenyl)propanol which has been used as a vasodilator.