188690-82-6

Basic information

• Product Name: (R)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol
• Synonyms: (R)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol;(R)-2-Bromo-1-(3-nitro-4-benzyloxyphenyl)ethanol;R-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol;BenzeneMethanol, a-(broMoMethyl)-3-nitro-4-(phenylMethoxy)-, (aR)-;(R)-1-(4-(benzyloxy)-3-nitrophenyl)-2-bromoethan-1-ol
• CAS NO: 188690-82-6
• Molecular Formula: C₁₅H₁₄BrNO₄
• Molecular Weight: 352.18
• Product Categories: API intermediates
• Mol File: 188690-82-6.mol

Chemical Properties

• Melting Point: 69-70 °C
• Boiling Point: 493.9 °C at 760 mmHg
• Flash Point: 252.5 °C
• Appearance: /
• Density: 1.529
• Vapor Pressure: 1.43E-10mmHg at 25°C
• Refractive Index: 1.638
• PKA: 12.21±0.20(Predicted)
• CAS DataBase Reference: (R)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol(188690-82-6)
• EPA Substance Registry System: (R)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol(188690-82-6)

Safety Data

• Hazardous Substances Data: 188690-82-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(R)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol is used as a building block in organic synthesis for the creation of other chemical compounds. Its unique structure and functional groups make it a valuable intermediate in the synthesis of complex organic molecules, potentially leading to the development of new pharmaceuticals, agrochemicals, or specialty chemicals.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (R)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol is used as a research compound for exploring its potential therapeutic applications. Its specific spatial arrangement and functional groups may confer unique biological activities, making it a candidate for further investigation in drug discovery programs. Researchers may study its interactions with biological targets, such as enzymes, receptors, or other proteins, to understand its potential as a therapeutic agent.
Used in Chemical Research:
(R)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol is also used in chemical research to investigate its properties and reactivity. Scientists may explore its potential as a catalyst, ligand, or other functional component in various chemical processes. Understanding its behavior in different chemical environments can provide insights into its potential applications and help develop new synthetic strategies or methodologies.

InChI:InChI=1/C15H14BrNO4/c16-9-14(18)12-6-7-15(13(8-12)17(19)20)21-10-11-4-2-1-3-5-11/h1-8,14,18H,9-10H2/t14-/m0/s1

Upstream product

• 170688-01-4 2-bromo-1-[4-fluoro-3-[(methylsulfonyl)amino]phenyl]ethanone 
• 79406-59-0 2-bromo-1-[4-chloro-3-[(methylsulfonyl)amino]phenyl]ethanone 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 6322-56-1 4'-hydroxy-3'-nitroacetophenone 
• 39258-98-5 2-bromo-1-[4-(benzyloxy)-3-(dimethylsulfamoylamino)phenyl]ethanone 
• 43229-01-2 4-benzyloxy-3-nitrophenacyl bromide 
• 14347-05-8 4-benzyloxy-3-nitroacetophenone 

Downstream Products

• 201677-59-0 N-[5-((1R)-2-bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]carboxamide 
• 861448-71-7 N-[2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methane sulfonamide 
• 861448-79-5 (3-{2-[(2R)-2-(4-benzyloxy-3-methanesulfonylaminophenyl)-2-(tert-butyldimethylsilanyloxy)ethylamino]-2-methylpropyl}phenyl)acetic acid methyl ester 
• 861448-88-6 methyl (3-{2-[((2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-2-methylpropyl}phenyl)acetate 
• 861448-89-7 (3-{2-[(2R)-2-(tert-butyldimethylsilyloxy)-2-(4-hydroxy-3-methanesulfonylaminophenyl)ethylamino]-2-methylpropyl}phenyl)acetic acid 
• 862540-80-5 2-[3-(2-{[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl]amino}-2-methylpropyl)phenyl]-N-[(4'-hydroxybiphenyl-3-yl)methyl]acetamide 
• 861448-91-1 ethyl (3-{2-[((2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-{4-benzyloxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-2-methylpropyl}phenyl)acetate 
• 861448-92-2 ethyl (R)-2-(3-{2-[2-hydroxy-2-(4-benzyloxy-3-methanesulfonamidophenyl)ethylamino]-2-methylpropyl}phenyl)acetate 
• 861448-93-3 [3-(2-{[(2R)-2-{4-(benzyloxy)-3-[(methylsulfonyl)amino]phenyl}-2-hydroxyethyl]amino}-2-methylpropyl)phenyl]acetic acid 
• 170687-82-8 N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]phenyl}methane sulfonamide 
• 201677-57-8 N-[2-(benzyloxy)-5-[(2R)-oxiran-2-yl]phenyl]formamide 
• 1361398-82-4 N-(5-(2-((2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)butyl)amino)-1-hydroxyethyl)-2-hydroxyphenyl)formamide 

Relevant articles and documents

An efficient enantioselective synthesis of (R,R)-formoterol, a potent bronchodilator, using lipases

The potent β2-adrenergic receptor agonist formoterol (R,R)-1 has been obtained in enantiomerically pure form by a convenient chemoenzymatic approach by coupling of epoxide (R)-6 with the unprotected primary amine (R)-9. Both chiral precursors have been prepared by enantiodifferentiation processes involving Pseudomonas cepacia (lipase PS) and Candida antarctica lipase (CALB), respectively. For the resolution of amine 9, we have found that utilization of triethylamine as non-reactive base enhances the reaction rate and the enantioselectivity of the process. The key coupling reaction of (R)-6 and (R)-9 has been conducted through derivatization of the amine with the labile trimethylsilyl group, which liberates the amino group of the resulting amino alcohol (R,R)-11 upon column chromatography purification. In this way, the overall approach is shorter than others previously described. Copyright (C) 2000 Elsevier Science Ltd.

Conformational toolbox of oxazaborolidine catalysts in the enantioselective reduction of α-bromo-ketone for the synthesis of (R,R)- formoterol

Several conformationally constrained oxazaborolidine catalysts have been evaluated in the reduction of ketone I. Readily accessible (1R, 2S) 1-amino- 2-tetralol (B-H) derived oxazaborolidine catalyst (6b) proves to be the most effective and practical catalyst in the reduction of bromo-ketone 1 (96% ee).

Diethylanilineborane: A practical, safe, and consistent-quality borane source for the large-scale enantioselective reduction of a ketone intermediate in the synthesis of (R,R)-formoterol

The development of a process for the use of N,N-diethylaniline - borane (DEANB) as a borane source for the enantioselective preparation of a key intermediate in the synthesis of (R,R)-formoterol L-tartrate, bromohydrin 2, from ketone 3 on kilogram scale is described. DEANB was found to be a more practical, safer, and higher-quality reagent when compared to other more conventional borane sources: borane - THF and borane - DMS.

Method for synthesizing arformoterol free alkali

The invention discloses a method for synthesizing arformoterol free alkali, which comprises the following steps of: (1) performing carbonyl chiral reduction reaction on a compound shown as a formula SM1 serving as a raw material in a first solvent to obtain a reaction solution containing a compound shown as a formula M1, and concentrating to dryness; (2) dissolving the material obtained in the step (1) with a second solvent, carrying out a hydrogenation reaction to obtain a reaction liquid containing a compound represented by a formula M2, filtering the reaction liquid, and cooling the filtrate; (3) carrying out formylation reaction on the filtrate cooled in the step (2) to obtain a reaction solution containing a compound as shown in a formula M3, and concentrating to dryness; (4) dissolving the material obtained in the step (3) with a third solvent, carrying out a cyclization reaction to obtain a reaction liquid containing a compound represented by a formula M4 and free SM2, filtering, and concentrating the filtrate to dryness; and (5) dissolving the material obtained in the step (4) with a fourth solvent, carrying out a condensation reaction to obtain an arformoterol precursor represented by a formula M5, and carrying out hydrogenation debenzylation on the M5 to obtain arformoterol.

Preparation method of formoterol key intermediate

The invention provides a preparation method of a formoterol key intermediate (R)-N-(2-(benzyloxy)-5-(2-bromo-1-hydroxyethyl)phenyl)formamide represented by a formula I, wherein asymmetric reduction isperformed by using 1-(4-(benzyloxy)-3-nitrophenyl)-2-bromoethanone (II) as a raw material and using (3aS-cis)-(-)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazole-2-isopropylborane (IV) as a catalyst toobtain a chiral alcohol intermediate (R)-1-(4-(benzyloxy)-3-nitrophenyl)-2-bromoethanol (III) with high enantioselectivity, and then nitro reduction and formylation one-pot reaction are performed to obtain a target product represented by the formula I. Compared with the traditional resolution method, the method of the invention has advantages of high chiral purity of the product, short productionperiod, easy operation, mild condition, convenient post-treatment and high yield, and is suitable for large-scale industrial production.

CLASS OF BIFUNCTIONAL COMPOUNDS WITH QUATERNARY AMMONIUM SALT STRUCTURE

The invention provides a class of compounds represented by formula (I), having bifunctional active quaternary ammonium salt structure of a β2-adrenoreceptor agonist and an M receptor antagonist, a pharmaceutically acceptable salt, solvate, and optical isomer thereof. A pharmaceutical composition comprising such a compound with quaternary ammonium salt structure, a method for preparing such a compound with quaternary ammonium salt structure and an intermediate thereof, and uses thereof in treating pulmonary disorders are also provided. The compounds of the invention have high selectivity to the M receptor subtype, and have less adverse reaction and lower toxic and side effects in the treatment of pulmonary diseases such as COPD and asthma.

(S) or (R)-diphenyl-pyrrolidine methanol immobilized by pentaerythritol and its preparation method and application

The invention discloses a (S/R)-diphenyl-pyrrolidine methanol immobilized by pentaerythritol and its preparation method and application. The (S/R)-diphenyl-pyrrolidine methanol is shown as Formula (I). The preparation of the catalyst includes steps of reacting pentaerythritol with paratoluensulfonyl chloride to obtain pentaerythritol sulphonate; reacting with sodium azide to obtain pentaerythritecompound; reacting (S/R)-N-Cbz-4-hydroxyproline methyl ester with propargyl bromide to obtain (S/R)-N-Cbz-4-acetylene methoxy proline methyl ester; then reacting with chlorophenylmagnesium to obtain (S/R)-diphenyl-pyrrolidine methanol immobilized by pentaerythritol. The (S/R)-diphenyl-pyrrolidine methanol immobilized by pentaerythritol can be applied to the reaction of asymmetrical transformationand generation of prochiral phenyl ketones to be (R/S)- secondary alcohol; the catalyst can be recycled.

PROCESS FOR THE PREPARATION OF ARFORMOTEROL OR SALT THEREOF

Provided is an improved process for the preparation of arformoterol L-(+)-tartrate, and more specifically provided is a novel process for the preparation of arformoterol L-(+)-tartrate via arformoterol D-(?)-tartrate.

Design, synthesis and evaluation of dual pharmacology β2- adrenoceptor agonists and PDE4 inhibitors

A novel series of formoterol-phthalazinone hybrids were synthesised and evaluated as dual pharmacology β2-adrenoceptor agonists and PDE4 inhibitors. Most of the hybrids displayed high β2-adrenoceptor agonist and moderate PDE4 inhibitory activities. The most potent compound, (R,R)-11c, exhibited agonist (EC50 = 1.05 nM, pEC50 = 9.0) and potent PDE4B2 inhibitory activities (IC50 = 0.092 μM).

Dual β2-adrenoceptor agonists-PDE4 inhibitors for the treatment of asthma and COPD

We designed and synthesized a novel class of dual pharmacology bronchodilators targeting both b2-adrenoceptor and PDE4 by applying a multivalent approach. The most potent dual pharmacology molecule, compound 29, possessed good inhibitory activity on PDE4B2 (IC50 = 0.278 μM, which was more potent than phthalazinone, IC50 = 0.520 lM) and possessed excellent relaxant effects on tracheal rings precontracted by histamine (pEC50 = 9.3).