193761-53-4

Usage

Uses

An intermediate in synthesis of (R,R)-Formoterol.

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-/m1/s1

Upstream product

• 43229-01-2 4-benzyloxy-3-nitrophenacyl bromide 
• 100-44-7 benzyl chloride 
• 14347-05-8 4-benzyloxy-3-nitroacetophenone 
• 6322-56-1 4'-hydroxy-3'-nitroacetophenone 

Downstream Products

• 188730-96-3 (S)-4-benzyloxy-3-nitrostyrene oxide 
• 1361398-83-5 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 
• 306966-56-3 N-(2-(benzyloxy)-5-((S)-2-bromo-1-hydroxyethyl)phenyl)formamide 
• 1122063-33-5 (1S)-1-(3-amino-4-benzyloxyphenyl)-2-bromoethan-1-ol 
• 289657-25-6 (S)-1-(3-Amino-4-benzyloxy-phenyl)-2-{benzyl-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethyl]-amino}-ethanol 
• 67346-49-0 (S,S)-formoterol 
• 67346-50-3 (S,R)-Formoterol 

Relevant academic research and scientific papers

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).

Corey-itsuno reduction of ketones: A development of safe and inexpensive process for synthesis of some API intermediates

A safe and inexpensive procedure for asymmetric reduction of ketones using in situ prepared N,N-diethylaniline borane (DEANB) and oxazaborolidine catalyst from sodium borohydride, N,N-diethylaniline hydrochloride and (S)-α,α-diphenylprolinol is described. This protocol is demonstrated successfully to manufacture enantiopure dapoxetine at the plant scale.

The asymmetric synthesis of (R,R)-formoterol via transfer hydrogenation with polyethylene glycol bound Rh catalyst in PEG2000 and water

(R,R)-formoterol was synthesized in seven steps with 4-hydroxyl-3-nitro- acetophenone as the starting material. The key intermediate, the chiral secondary alcohol 4, was prepared via Rh-catalyzed asymmetric transfer hydrogenation with (S,S)-PEGBsDPEN as the ligand and sodium formate as the hydrogen donor under mild conditions. With a mixture of PEG 2000 and water as the reaction media, the catalyst system could be recycled four times.

ACETAMIDE STEREOISOMER

The compound of formula (I)is a water-stable, long acting β2-selective adrenoceptor agonist useful as a bronchodilator in the treatment of bronchoconstriction associated with reversible obstructive airways diseases and the like.

Carbamate Stereoisomer

The compound of formula (I) is a water-stable, long acting β2-selective adrenoceptor agonist useful as a bronchodilator in the treatment of bronchoconstriction associated with reversible obstructive airways diseases and the like.

Asymmetric transfer hydrogenation of ketones catalyzed by hydrophobic metal-amido complexes in aqueous micelles and vesicles

Asymmetric transfer hydrogenation of ketones, especially α-bromomethyl aromatic ketones, catalyzed by unmodified, hydrophobic transition metal-amido complexes (TsDPEN-M), was performed successfully with significant enhancement of activity, chemoselectivity, and enantio-selectivity (up to 99% ee) in aqueous media containing micelles and vesicles. The hydrophobic catalyst, embedded in micelles constructed from the surfactant cetyltrimethylammonium bromide (CTAB), could be separated from the organic phase along with the products and was recycled for at least six times.

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.

Large-scale synthesis of enantio- and diastereomerically pure (R,R)-formoterol

(R,R)-Formoterol (1) is a long-acting, very potent β2-agonist, which is used as a bronchodilator in the therapy of asthma and chronic bronchitis. Highly convergent synthesis of enantio- and diastereomerically pure (R,R)-formoterol fumarate is achieved by a chromatography-free process with an overall yield of 44%. Asymmetric catalytic reduction of bromoketone 4 using as catalyst oxazaborolidine derived from (1R, 2S)-1-amino-2-indanol and resolution of chiral amine 3 are the origins of chirality in this process. Further enrichment of enantio- and diastereomeric purity is accomplished by crystallizations of the isolated intermediates throughout the process to give (R,R)-formoterol (1) as the pure stereoisomer (ee, de >99.5%).

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).

Enantio- and diastereoselective synthesis of all four stereoisomers of formoterol

Enantioselective syntheses of all four stereoisomers of formoterol are accomplished using asymmetric catalytic borane reductions with chiral oxazaborolidines as reducing agents.