29261-25-4

Upstream product

• 75-31-0 isopropylamine 
• 27993-71-1 1-(2-chlorophenyl)-2-hydroxyethanone 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 23496-56-2 (+/-)-2-amino-1-(2-chlorophenyl)ethanol 
• 67-64-1 acetone 
• 5000-66-8 2-chlorophenacyl bromide 
• 855300-90-2 C₁₀H₈ClNO₃ 
• 3811-25-4 clorprenaline 
• 62717-50-4 o-chlorostyrene oxide 
• 6933-90-0 Clorprenaline hydrochloride 
• 4209-25-0 2-chloro-1-(2-chlorophenyl)ethanone 
• 62717-50-4 (R)-(-)-2-(2-chlorophenyl)oxirane 

Relevant academic research and scientific papers

Preparation of a novel hydroxypropyl-γ-cyclodextrin functionalized monolith for separation of chiral drugs in capillary electrochromatography

In this study, a novel hydroxypropyl-γ-cyclodextrin (HP-γ-CD) functionalized monolithic capillary column was prepared by one-pot sequential strategy and used for chiral separation in capillary electrochromatography for the first time. In one pot, GMA-HP-γ-CD as functional monomer was allowed to be formed via the ring opening reaction between HP-γ-CD and glycidyl methacrylate (GMA) catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and then copolymerized directly with ethylene dimethacrylate (EDMA) and 2-acrylamido-2-methyl propane sulfonic acid (AMPS) in the presence of porogenic solvents via thermally initiated free radical polymerization. The preparation conditions of monoliths were optimized. Enantiomer separations of six chiral drugs including pindolol, clorprenaline, tulobuterol, clenbuterol, propranolol, and tropicamide were achieved on the monolith. Among them, pindolol, clorprenaline, and tropicamide were baseline separated with resolution values of 1.62, 1.73, and 1.55, respectively. The mechanism of enantiomer separation was discussed by comparison of the HP-γ-CD and HP-β-CD functionalized monoliths.

Preparation method of stable isotope-labeled clorprenaline

The invention relates to a preparation method of stable isotope-labeled clorprenaline. The preparation method comprises the following steps: with 2-bromo-2'-chloroacetophenone as an initial raw material, successively conducting improved Gabriel synthesis (wherein the initial raw material and an amination reagent sodium, namely diformyl amide are subjected to a nucleophilic substitution reaction), hydrolysis, reduction and reductive amination so as to synthesize the isotope-labeled clorprenaline . According to the preparation method disclosed by the invention, through a four-step conventional chemical reaction, process design is reasonable, raw material price is low, an experimental process is controllable, operation is simple and convenient, various required labeled compounds such as D-labeled, 13C-labeled or D/13C double-labeled compounds can be conveniently synthesized, the purity of the prepared target product is high and reaches 98% or above, total yield reaches 66% or above, the isotope abundance of the final product can reach 98% or above, the phenomenon of isotope abundance dilution is avoided, higher reproducibility and stability are achieved, and the obtained target compound can provide a standard reagent for accurately and quantitatively detecting trace residues of clorprenaline.

Method for preparing beta-arylamino alcohol drugs such as tulobuterol, clorprenaline, dichloroisoprenaline and sotalol

The invention provides a method for preparing beta-arylamino alcohol drugs such as tulobuterol, clorprenaline, dichloroisoprenaline and sotalol. The beta-arylamino alcohol drugs have a chemical structure represented by a formula 4 shown in the description. The method comprises the following steps: (1) reacting arylethanone represented by a formula 1 shown in the description with a halogenating agent and sulfoxide to obtain arylglyoxal represented by a formula 2 shown in the description and or 1,1-dihydroxyarylethanone represented by a formula 3 shown in the description; and (2) performing a nucleophilic addition reaction on the arylglyoxal represented by the formula 2 and/or the 1,1-dihydroxyarylethanone represented by the formula 3 and an amine compound having a chemical formula of R1-NH2, and performing a reductive amination reaction in the presence of a reducing agent to obtain the beta-arylamino alcohol drugs.

Comparison of three S-β-CDs with different degrees of substitution for the chiral separation of 12 drugs in capillary electrophoresis

Three kinds of sulfated β-cyclodextrin (S-β-CD), including a single isomer, heptakis-6-sulfato-β-cyclodextrin (HS-β-CD), degree of substitution (DS) of 7, which was synthesized in our laboratory and another two commercialized randomly substituted mixtures, a sulfated β-cyclodextrin with DS of 7 to 11, as well as a highly sulfated-β-cyclodextrin with DS of 12 to 15, were used for the enantioresolution of 12 drugs (the β-blockers, phenethylamines, and anticholinergic agents) in capillary electrophoresis. The enantioseparation under varying concentrations of S-β-CD and background electrolyte pH were systematically investigated and compared. Based on the experimental results, the effect of the nature of S-β-CD and analyte structure on the enantioseparation is discussed.

Method for preparing clorprenaline optical isomers based on chiral liquid chromatography

The invention provides a method for preparing clorprenaline optical isomers based on chiral liquid chromatography, comprising the specific steps: 1), preparing a sample; 2) determining chiral chromatographic separation conditions, and preparing under medium pressure; 3), collecting optical isomers respectively, and lyophilizing; 4), measuring purity of the optical isomers. Chiral liquid chromatography is selected to prepare clorprenaline optical isomers for the purpose of solving the problem that synthesis of optically pure clorprenaline in actual scientific research and production is high in difficulty and high in preparation cost, preparation of optical isomers is available for both clorprenaline and its salts, the method has the advantages of good operation simplicity, high preparation efficiency, low cost, high optical purity and the like, the method is applicable particularly to the preparation of high-performance low-toxicity optically pure clorprenaline required by medical industry, corresponding quality control standards may be established for preparation, the method is more widely applicable, and a new concept and method is provided for the research and development, production and quality control for optically pure clorprenaline.

The Ru-catalyzed enantioselective preparation of chiral halohydrins and their application in the synthesis of (R)-clorprenaline and (S)-sotalol

The asymmetric transfer hydrogenation of a series of halo-substituted aryl methyl ketones, including those substituted in both α-methyl and aryl rings, was studied for the preparation of chiral halohydrins. Up to 99.7% ee was obtained with 2-chloro-1-(2-chlorophenyl)ethanone as the substrate and Ru-CsDPEN as the catalyst in an HCOONa/H2O system. (R)-Clorprenaline, a drug used in the treatment of respiratory disorders, such as bronchitis and asthma, and (S)-sotalol, a class-III antiarrhythmic compound, were prepared with these chiral halohydrins.

anti-Prelog microbial reduction of aryl α-halomethyl or α- hydroxymethyl ketones with Geotrichum sp. 38

Reduction of aryl α-halomethyl ketones 5a-d and 7a-h and α- hydroxymethyl ketones 10a-b by Geotrichum sp. 38 affording mostly the anti- Prelog alcohols was reported and the stereoselectivities of the reductive products were discussed.

Aminoalcohols, III: Preparation of Enantiomerically Pure Pharmacologically Active N-Substituted β-Aminoalcohols

A synthesis of N-substituted β-aminoalcohols is described starting from enantiomerically pure O-MBF- or O-MBE-protected β-aminoalcohols which can be prepared via LiAlH4 reduction of O-protected cyanohydrines. - Keywords: 1,2-Amino-alcohols, enantiomerically pure; N-Alkylation; Clorprenaline; Propranolol; Midodrine