18672-08-7

Upstream product

• 6111-99-5 ethyl diazoalaninate 
• 106-48-9 4-chloro-phenol 
• 1193-00-6 sodium 4-chlorophenolate 
• 687-47-8 (S)-Ethyl lactate 

Downstream Products

• 545375-98-2 (+)-(S)-4-methyl-1-[2-(4-chlorophenoxy)-1-oxopropyl]piperidine 
• 3307-39-9 (S)-2-(4-chlorophenoxy)propionic acid 

Relevant academic research and scientific papers

Planar chiral [2.2]paracyclophane-based bisoxazoline ligands: Design, synthesis, and use in cu-catalyzed inter- and intramolecular asymmetric O-H insertion reactions

Centrally chiral bisoxazolines connected directly to a planar chiral [2.2]paracyclophane backbone were synthesized and evaluated as asymmetric ligands in Cu-catalyzed intermolecular ethanolic O-H insertion reactions of α-diazo esters. The reactivities and enantioselectivities of Cu complexes of the synthesized bisoxazoline ligands were lower than those of ligands without central chirality. However, planar chiral [2.2] paracyclophane-based bisoxazoline ligands with an inserted benzene spacer that had a sterically demanding isopropyl substituent showed good enantioselectivities in inter- and intramolecular aromatic O-H insertion reactions, without the aid of central chirality.

PROCESS FOR PREPARING (R)-ARYLOXYPROPIONIC ACID ESTER DERIVATIVES

The present invention relates to a method for preparing optically active (R)-aryloxypropionic acid ester derivatives, and more particularly to a method for preparing (R)- aryloxypropionic acid ester derivatives with high optical purity and good yield at low cost from phenol derivatives with various substituted functional groups and (S)-alkyl O-arylsulfonyl lactates.

Synthesis of chiral 1-[ω(4-chlorophenoxy)alkyl]-4-methylpiperidines and their biological evaluation at σ1, σ2, and sterol δ8-δ7 isomerase sites

Sumitomo's patented σ ligand 1-[3-(4-chlorophenoxy)propyl]-4-methylpiperidine (15), which has been claimed as agent for CNS disorders and neuropathies, and its lower homologue 12 were prepared along with related chiral (4-chlorophenoxy)alkylpiperidines. They were tested at σ1, σ2, and sterol Δ8-Δ7 isomerase (SI) sites by in vitro radioligand binding assays, to evaluate the influence of a chiral center in the alkyl chain on the selective σ1 binding relative to other σ family sites. Generally high σ1-site affinities were found, so that the chirality introduced by a methyl substitution resulted in slight differences. Nevertheless, the shorter oxyethylenic chain was beneficial to increase σ1 selectivity. However, the (-)-(S)-4-methyl-1-[2-(4-chlorophenoxy)1-methylethyl]piperidine ((-)-(S)-17) reached the highest σ1 affinity (Ki = 0.34 nM) and the best selectivity relative to the σ2 site (547-fold). Compound (-)-(S)-17 displayed also a moderate selectivity (11-fold) relative to the SI site.