56141-72-1

Upstream product

• 86-21-5 pheniramine 
• 50-00-0 formaldehyd 
• 67-56-1 methanol 
• 15260-65-8 2-(1-phenylvinyl)pyridine 
• 7541-17-5 tert-butyl N,N-dimethylcarbamate 

Relevant academic research and scientific papers

Conjugate Addition-Enantioselective Protonation of N-Aryl Glycines to α-Branched 2-Vinylazaarenes via Cooperative Photoredox and Asymmetric Catalysis

An enantioselective protonation strategy has been successfully applied to the synthesis of chiral α-tertiary azaarenes. With a dual catalytic system involving a chiral phosphoric acid and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer that is mediated by visible light, a variety of α-branched 2-vinylpyridines and 2-vinylquinolines with N-aryl glycines underwent a redox-neutral, radical conjugate addition-protonation process and provided valuable chiral 3-(2-pyridine/quinoline)-3-substituted amines in high yields with good to excellent enantioselectivities (up to >99% ee). An application of this methodology to a two-step synthesis of the enantiomerically pure medicinal compound pheniramine (Avil) is also presented.

Conjugate addition-enantioselective protonation to forge tertiary stereocentres α to azaarenes via cooperative hydrogen atom transfer and chiral hydrogen-bonding catalysis

Cooperative hydrogen atom transfer and chiral hydrogen-bonding catalysis as a new platform for the asymmetric synthesis of azaarene derivatives is reported. By using a tetrabutylammonium decatungstate as the photocatalyst and a chiral phosphoric acid as the hydrogen-bonding catalyst, transformations of a variety of commercially available hydrocarbons and silanes with diverse α-branched 2-vinylazaarenes could efficiently experience a tandem radical conjugate addition and enantioselective protonation process, providing a convenient and fully atom economical approach to access a range of valuable enantioenriched α-tertiary azaarenes in high yields with good to excellent enantioselectivities (up to 93% ee). Through the direct use of tert-butyl methylcarbamate as the feedstock, this method enables a highly practical and concise synthesis of the enantiomerically pure medicinal molecule pheniramine (Avil).

Visible light asymmetric catalytic synthesis method of chiral 3-(2-pyridine)-3-aryl substituted amine compound

The invention relates to a visible light asymmetric catalytic synthesis method of a chiral 3-(2-pyridine)-3-aryl substituted amine compound. The synthesis route is as shown in the specification, the structures of chiral spiro phosphonic acid and DPZ are as shown in the specification, under argon atmosphere, N-aryl substituted glycine (I) and alpha-aryl-alpha-(2-pyridine) substituted terminal olefin (II) are completely reacted at-35 to-40 DEG C under visible light irradiation in the presence of the DPZ, lithium hexafluorophosphate and the chiral spiro phosphonic acid as catalysts in THF or toluene to obtain a target chiral amine compound (III) through column chromatography separation and purification, wherein in the compounds I, II and III, R1 is CN, H, F, Cl, Br, Ph or Me, R2 is H, Me, Clor Br, and R3 is H, F, Cl, Br, Me or MeO. The compound shown in the formula III is the chiral 3-(2-pyridine)-3-aryl substituted amine compound.

Enantiomeric separation and simulation studies of pheniramine, oxybutynin, cetirizine, and brinzolamide chiral drugs on amylose-based columns

Solid phase extraction (SPE)-chiral separation of the important drugs pheniramine, oxybutynin, cetirizine, and brinzolamide was achieved on the C 18 cartridge and AmyCoat (150 x 46 mm) and Chiralpak AD (25 cm x 0.46 cm id) chiral columns in hum

Synthesis of dendrimer-type chiral stationary phases based on the selector of (1S,2R)-(+)-2-amino-1,2-diphenylethanol derivate and their enantioseparation evaluation by HPLC

In our recent work, a series of dendritic chiral stationary phases (CSPs) were synthesized, in which the chiral selector was L-2-(p-toluenesulfonamido)-3- phenylpropionyl chloride (selector I), and the CSP derived from three-generation dendrimer showed the best separation ability. To further investigate the influence of the structures of dendrimer and chiral selector on enantioseparation ability, in this work, another series CSPs (CSPs 1-4) were prepared by immobilizing (1S,2R)-1,2-diphenyl-2-(3-phenylureido)ethyl 4-isocyanatophenylcarbamate (selector II) on one- to four-generation dendrimers that were prepared in previous work. CSPs 1 and 4 demonstrated the equivalent enantioseparation ability. CSPs 2 and 3 showed the best and poorest enantioseparation ability respectively. Basically, these two series of CSPs exhibited the equivalent enantioseparation ability although the chiral selectors were different. Considering the enantioseparation ability of the CSP derived from aminated silica gel and selector II is much better than that of the one derived from aminated silica gel and selector I, it is believed that the dendrimer conformation essentially impacts enantioseparation.