1199945-26-0

Basic information

• Product Name: N-Benzyl (-)-Nebivolol
• Synonyms: N-Benzyl (-)-Nebivolol;(αS,α'S,2R,2'S)-α,α'-[[(PhenylMethyl)iMino]bis(Methylene)]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-Methanol
• CAS NO: 1199945-26-0
• Molecular Formula: C₂₉H₃₁F₂NO₄
• Molecular Weight: 495.5575464
• Product Categories: Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1199945-26-0.mol

Chemical Properties

• Boiling Point: 654.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.286±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.24±0.20(Predicted)
• CAS DataBase Reference: N-Benzyl (-)-Nebivolol(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzyl (-)-Nebivolol(1199945-26-0)
• EPA Substance Registry System: N-Benzyl (-)-Nebivolol(1199945-26-0)

Safety Data

• Hazardous Substances Data: 1199945-26-0(Hazardous Substances Data)

Usage

Chemical Properties

Brown Semisolid

Uses

(-)-Nebivolol intermediate.

Upstream product

• 129050-26-6 (2R)-6-fluoro-2-[(2S)-oxiran-2-yl]-3,4-dihydro-2H-chromene 
• 100-46-9 benzylamine 
• 129050-27-7 (R)-2-benzylamino-1-((S)-6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanol 
• 197706-50-6 6-fluoro-(2R)-2-[(2R)-2-oxiranyl]-3,4-dihydrobenzopyran 
• 303176-43-4 1-[6-fluoro-(2R)-3,4-dihydro-2H-benzopyran-2-yl]-(1S)-1,2-ethylene glycol 
• 1322622-97-8 2-(benzylamino)-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanol 
• 1345202-57-4 (2S)-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-hydroxyethyl-2,2-dimethylpropanoate 
• 1345202-60-9 (2S)-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-tosyloxyethyl-2,2-dimethylpropanoate 
• 1345202-52-9 (2S)-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-hydroxyethyl acetate 
• 1345202-53-0 (2S)-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-{[(4-methylphenyl)sulfonyl]oxy}ethyl acetate 
• 129050-23-3 (2S)-6-fluoro-2-[(2S)-oxiran-2-yl]-3,4-dihydro-2H-chromene 
• 1322623-11-9 1-(6-fluorochroman-2-yl)ethane-1,2-diol 
• 99199-61-8 C₁₂H₁₃FO₃ 
• 1219914-99-4 2-chloro-1-[(2R)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]ethan-1-one 

Downstream Products

• 152520-56-4 nebivolol hydrochloride 
• 152520-56-4 DL-nebivolol hydrochloride 

Relevant articles and documents

Synthesis of intermediate compound and [...] (by machine translation)

Synthesis of intermediate compounds [a] and [...]. [Solution] a [...], asymmetric epoxidation, sulfonyl halide in the presence of base catalyst by sulfonation, alkylation of amines, such as synthesized by a series of cross-coupling reaction. [Effect] [...] important from the viewpoint of pharmacological value, high efficiency, low cost, and which meets the requirements of industrial, optical isomers may be prepared [...] and develop a method, which is very economical in social benefit. [Drawing] no (by machine translation)

Nebivolol synthetic method and intermediate compounds of the

The present invention relates to a synthesis method and an intermediate compound of nebivolol. Specifically the invention relates to the method for synthesizing the nebivolol, the intermediate compound of the nebivolol, and a method for preparing the intermediate compound.

PROCESS FOR THE SYNTHESIS OF INTERMEDIATES OF NEBIVOLOL

The present invention relates to a novel process for the synthesis of the intermediate compounds constituted by chromanyl haloketones of formula III and 6-fluoro-2-(oxiran-2-yl) chromans of formula I. The intermediates thus obtained can be used for the sy

A PROCESS FOR THE PREPARATION OF 6-FLUORO-3,4-DIHYDRO-2H-CHROMENE- 2-CARBALDEHYDE

The present invention relates to a process for ihe preparation of 6-f!uoro-3,4-dihydro- 2H-chromene-2-carbaidehyde which is useful as an Intermediate in the synthesis of Nebivolol or its pharmaceutical acceptable salts.

METHOD FOR PRODUCING NEBIVOLOL

The present invention relates to a method for producing racemic nebivolol represented by general formula (I) from the enantiomerically-pure compounds represented by formula (IVa) and (IVb); whereby racemic nebivolol is obtained through mixing enantiomerically-pure d-nebivolol and l-nebivolol which are synthesised independent of each other as enantiomerically-pure compounds through individual coupling of the 4 enantiomerically-pure key intermediates represented by formula (IIa-d) to the corresponding precursors represented by formula (IIIa-d); whereby d-nebivolol (Ia) is obtained through coupling (IIa) to (IIIb) or (IIb) to (IIIa) and l-nebivolol (Ib) is obtained through coupling (IIc) to (IIId) or (IId) to (IIIc), and PG in the intermediates represented by formula (IIa-d) is a hydrogen atom or an amine protection group, and X in the precursors represented by formula (IIIa-d) is a halogen atom, a hydroxyl group, an acyl group, an alkylsulfonyloxy group or an arylsulfonyloxy group, whereby intermediate (IIa) is formed from (IIIa), intermediate (IIb) is formed from (IIIb), intermediate (IIc) is formed from (IIIc), and intermediate (IId) is formed from (IIId), whereby the precursors represented by formula (IIIa) and (IIId) originate from the ketone precursor represented by formula (IVa), and the precursors represented by formula (IIIb) and (IIIc) originate from the ketone precursor represented by formula (IVb), and Z in the ketone precursors (IVa,b) is a halogen atom, a hydroxyl function, an acyl group, an alkylsulfonyloxy group or an arylsulfonyloxy group.

PROCESS FOR THE PREPARATION OF EPOXIDES AS INTERMEDIATES FOR THE SYNTHESIS OF NEBIVOLOL

The present invention relates to a novel process of synthesis of epoxides, 6-fluoro-2- (oxiran-2-yl) chroman (Figure 1), intermediates for the synthesis of nebivolol, depicted in Scheme (1), enabling to obtain the above- mentioned epoxides in a racemic or semichiral form.

PROCESS FOR THE PREPARATION OF NEBIVOLOL

The present invention relates to a novel process for the synthesis of the Nebivolol product depicted in Scheme 1, comprised of a reduced number of high-yield steps, and characterized by the enzymatic resolution of the chroman ester precursor.

PROCESS FOR THE CONVERSION OF (2R)-6-FLUORO-2-[(2S)-OXIRAN-2-YL]-3,4-DIHYDRO-2H-CHROMENE TO (2R)-6-FLUORO-2-[(2R)-OXIRAN-2-YL]-3,4-DIHYDRO-2H-CHROMENE

The present invention relates to a novel process for the conversion of (2R)-6-fluoro- 2-[(2S)-oxiran-2-yl]-3,4-dihydro-2H-chromene (formula lll-A) to (2R)-6-fluoro-2-[(2R)-oxiran- 2-yl]-3,4-dihydro-2H-chromene (formula lll-B). The compound of formula lll-

PREPARATION OF NEBIVOLOL

Processes for the synthesis of pharmacologically active 2,2-iminobisethanol derivatives, e.g., 2H-1-benzopyran-2 methanol-α,α′-iminobis(methylene)]bis-[6-fluoro-3,4-dihydro-[2R*[R*[R*(S*)]]]], and their pharmaceutically acceptable salts.