113806-19-2Relevant academic research and scientific papers
SIMPLE PREPARATIONS OF SOME HYDANTOINS OF PHENYLALANINE AND α-MePhe AND THEIR CHIRAL STABILITY DURING N3-ALKYLATION. A ROUTE TO THE SYNTHESIS OF CHIRAL AMINES
Anteunis, M.J.O.,Spiessens, L.,Witte, M. De,Callens, R.,Reyniers, Fr.
, p. 459 - 466 (2007/10/02)
Preparations of chiral-pure hydantoins derived from L-Phe and L-α-MePhe are revisited.A one step quantitative route for 5-benzyl-5-methyl hydantoin is obtained by melting α-MePhe with ureum.L-Phe-hydantoin could not be alkylated at N-3 with conservation of chirality at C-5.Diastereomers resulting from asymmetric alkyl groupings implanted at N-3 can be separated by crystallization in aqueous medium.The N-3 alkylated hydantoins can be hydrolyzed in high yields with Ba(OH)2.This allows the preparation of enantiomeric pure amines such like 2-methylbutylamine and 2-hydroxypropylamine via N-3 alkylation of the chirally-stable hydantoin of α-MePhe followed by enantiomeric resolution and hydrolysis.
