HETEROCYCLES

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

■ 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

Abstract

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.