Synthesis of B-(sec-Amino)alanines

Nobuhiro ABE; Fumiko FUJISAKI; Kunihiro SUMOTO

doi:10.1248/cpb.46.142

Nobuhiro ABE, Fumiko FUJISAKI, Kunihiro SUMOTO

Author information

Keywords: ethyl hydrogen aminomalonate, 1-piperidinemethanol, Mannich reaction, hydrolysis, mechanism, diethyl formamidomalonate

JOURNAL FREE ACCESS

1998 Volume 46 Issue 1 Pages 142-144

DOI https://doi.org/10.1248/cpb.46.142

Details

Abstract

Preparation of β-(sec-amino)alanines (3) by acid hydrolysis of diethyl (sec-aminomethyl)formamidomalonates (2) was studied. Although high reaction temperature resulted in low yield, low reaction temperature (below 30°C) gave good to excellent yields. The hydrolysis of diethyl formamido(piperidinomethyl)malonate (2a) was followed by ¹H-NMR, and a plausible mechanism involving the condensation of ethyl hydrogen aminomalonate (7) with 1-piperidinemethanol (5) is proposed.

Corresponding author

Register with J-STAGE for free!