SYNTHESIS OF 2R)-1-(4-CHLORO-2-PYRIDYL)-2-(2-PYRIDYL)ETHYLAMINE - A SELECTIVE OXIME REDUCTION AND CRYSTALLIZATION-INDUCED ASYMMETRIC TRANSFORMATION

Authors
NEGI S MATSUKURA M MIZUNO M MIYAKE K MINAMI N
Citation
S. Negi et al., SYNTHESIS OF 2R)-1-(4-CHLORO-2-PYRIDYL)-2-(2-PYRIDYL)ETHYLAMINE - A SELECTIVE OXIME REDUCTION AND CRYSTALLIZATION-INDUCED ASYMMETRIC TRANSFORMATION, Synthesis, (8), 1996, pp. 991
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
8
Year of publication
1996
Database
ISI
SICI code
0039-7881(1996):8<991:SO2-AS>2.0.ZU;2-L
Abstract
Reduction of 1-(4-chloro-2-pyridyl)-2-(2-pyridyl)ethanone oxime (3) us ing zinc in trifluoroacetic acid gave the corresponding racemic pyridy lethylamine 4 in excellent yield without reductive removal of the chlo rine atom. A subsequent diastereomeric crystallization of the amine 4 with an optically active cis-cyclohexanecarboxylic acid derivative in the presence of a catalytic amount of 3,5-dichlorosalicylaldehyde was found to give the desired R-amine 6 in 42% yield via a ''crystallizati on-induced asymmetric transformation.''