180748-35-0

Upstream product

• 63071-13-6 4-chloro-2-pyridinecarbaldehyde 
• 100-58-3 phenylmagnesium bromide 
• 626-61-9 4-Chloropyridine 
• 100-52-7 benzaldehyde 
• 180748-36-1 (4-chloropyridin-2-yl)(phenyl)methanone 
• 19235-89-3 4-chloro-pyridine-2-carbonitrile 
• 63071-10-3 (4-chloropyridin-2-yl)methanol 

Downstream Products

• 180748-36-1 (4-chloropyridin-2-yl)(phenyl)methanone 
• 896139-40-5 (R)-(-)-4-chloro-2-(1-hydroxybenzyl)pyridine 
• 896139-41-6 (R)-(-)-1-(4-chloro-2-pyridinyl)benzyl acetate 

Relevant academic research and scientific papers

Biocatalytic preparation of optically active 4-(N,N-dimethylamino)pyridines for application in chemical asymmetric catalysis

4-Chloro-2-(1-hydroxybenzyl)pyridine and 4-chloro-2-(1-hydroxyalkyl)pyridines were obtained with moderate to excellent enantiomeric excesses and high isolated yields by bioreduction with Baker's yeast of the corresponding ketones. The resulting optically active alcohols were transformed into adequate DMAP derivatives, which have been applied in asymmetric catalytic processes as nucleophilic catalysts in the stereoselective chemical alkoxycarbonylation of 1-phenylethanol or as chiral ligands in the enantioselective addition of diethylzinc to benzaldehyde.

TMSCH2Li-LiDMAE: a new nonnucleophilic reagent for C-2 lithiation of halopyridines

A new superbasic reagent has been discovered by combining TMSCH2Li and LiDMAE in hexane. This reagent was found highly efficient for the C-2 lithiation of sensitive chloro- and fluoropyridines. The metallation occurred chemo- and regioselectively at 0 °C avoiding the nucleophilic addition or substrate degradation commonly obtained with other alkyllithiums even at lower temperatures.

Synthesis of (2R)-1-(4-chloro-2-pyridyl)-2-(2-pyridyl)ethylamine: A selective oxime reduction and crystallization-induced asymmetric transformation

Reduction of 1-(4-chloro-2-pyridyl)-2-(2-pyridyl)ethanone oxime (3) using zinc in trifluoroacetic acid gave the corresponding racemic pyridylethylamine 4 in excellent yield without reductive removal of the chlorine 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 'crystallization-induced asymmetric transformation'.