929706-85-4

Basic information

• Product Name: rac N-Benzyl Nebivolol
• Synonyms: rac N-Benzyl Nebivolol;α,α'-[[(PhenylMethyl)iMino]bis(Methylene)]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-Methanol
• CAS NO: 929706-85-4
• Molecular Formula: C₂₉H₃₁F₂NO₄
• Molecular Weight: 495.5575464
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 929706-85-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: rac N-Benzyl Nebivolol(CAS DataBase Reference)
• NIST Chemistry Reference: rac N-Benzyl Nebivolol(929706-85-4)
• EPA Substance Registry System: rac N-Benzyl Nebivolol(929706-85-4)

Safety Data

• Hazardous Substances Data: 929706-85-4(Hazardous Substances Data)

Usage

Chemical Properties

Pale Brown Semi-Solid

Uses

Protected Nebivolol.

Upstream product

• 99199-90-3 6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran 
• 99199-91-4 6-fluoro-3,4-dihydro-α-[[(phenylmethyl)amino]methyl]-2H-1-benzopyran-2-methanol 
• 99199-60-7 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid 
• 409346-73-2 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde 
• 99199-59-4 6-fluoro-4-oxo-4H-1-benzopyran-2-carboxylic acid 
• 99199-62-9 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol 
• 129050-27-7 (S*,R*)-(±)-α-[(benzylamino)methyl](6-fluoro-2-chromanyl)methanol 
• 793669-26-8 [1R*(R*)]-6-fluoro-3,4-dihydro-2-(oxiran-2-yl)-2H-chromene 
• 100-46-9 benzylamine 
• 99199-91-4 (+/-)-[1S*(R*)]-6-fluoro-3,4-dihydro-α-[[(phenylmethyl)amino]methyl]-2H-1-benzopyran-2-methanol 
• 99199-90-3 (+/-)-[1S*(S*)]-6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran 

Downstream Products

• 99200-09-6 nebivolol 
• 9920-09-6 α,α'-iminobis(methylene)bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol] hydrochloride 
• 118457-14-0 R 67142 
• 118457-16-2 nebivolol 
• 920299-33-8 (R)-1-((R)-6-Fluoro-chroman-2-yl)-2-[(S)-2-((R)-6-fluoro-chroman-2-yl)-2-hydroxy-ethylamino]-ethanol; hydrochloride 
• 152520-56-4 nebivolol hydrochloride 
• 99200-09-6 (+/-)-[2R*[1S*,5S*(S*)]]-α,α-[iminobis(methylene)]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol] 
• 169293-50-9 nebivolol hydrochloride 

Relevant articles and documents

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.

Process for preparation of racemic Nebivolol

A process of making racemic [2S*[R*[R*[R*]]]] and [2R*[S*[S*[S*]]]]-(±)α,α′-[iminobis(methylene)]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol] of the compound of the formula (I) and its pure [2S*[R*[R*[R*]]]]- and [2R*[S*[S*[S*]]]]-enantiomer compo

A NOVEL PROCESS FOR PREPARATION OF NEBIVOLOL INTERMEDIATES

The present invention relates to a process for separation of desired diastereomeric pair from a mixture of diastereomeric pairs thereby obtaining nebivolol intermediates. Thus, the mixture of (+)-[1S*(R*)]-6-fluoro-3,4-dihydro-α-[[(phenylmethyl)amino]methyl]-2H-1-benzopyran-2-methanol, (+)-[1S*(S*)]-6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran and ethanol is heated to reflux temperature and stirred for 8 hours at the same temperature to obtain (+)-[2R*[1S*,5S*(S*)]]+[2R*[1S*,5R*(R*)]]-α,α'-[phenylmethyliminobis(methylene)]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol]. Then the reaction mass is cooled to 10oC, the pH is adjusted to 2 with HCl gas and stirred for 45 minutes at 25oC to 30oC. Then the separated solid is filtered and dried to give (+)-[2R*[1S*,5S*(S*)]]-α,α'-[phenylmethyliminobis(methylene)]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2- methanol] hydrochloride salt, which can be converted into nebivolol.