197706-50-6

Basic information

• Product Name: 6-fluoro-(2R)-2-[(2R)-2-oxiranyl]-3,4-dihydrobenzopyran
• Synonyms: 6-fluoro-(2R)-2-[(2R)-2-oxiranyl]-3,4-dihydrobenzopyran
• CAS NO: 197706-50-6
• Molecular Weight: 194.206
• Mol File: 197706-50-6.mol

Chemical Properties

• Boiling Point: 291.7±40.0 °C(Predicted)
• Density: 1.299±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 6-fluoro-(2R)-2-[(2R)-2-oxiranyl]-3,4-dihydrobenzopyran(CAS DataBase Reference)
• NIST Chemistry Reference: 6-fluoro-(2R)-2-[(2R)-2-oxiranyl]-3,4-dihydrobenzopyran(197706-50-6)
• EPA Substance Registry System: 6-fluoro-(2R)-2-[(2R)-2-oxiranyl]-3,4-dihydrobenzopyran(197706-50-6)

Safety Data

• Hazardous Substances Data: 197706-50-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-fluoro-(2R)-2-[(2R)-2-oxiranyl]-3,4-dihydrobenzopyran is used as a key intermediate in the synthesis of Nebivolol, a β1-Adrenergic blocker. Nebivolol is a medication that is primarily used to treat hypertension (high blood pressure) and heart failure. The compound's unique structure allows for the development of drugs with specific targeting and blocking properties, making it an essential component in the creation of effective cardiovascular medications.
As an intermediate in the synthesis of Nebivolol, 6-fluoro-(2R)-2-[(2R)-2-oxiranyl]-3,4-dihydrobenzopyran plays a significant role in the pharmaceutical industry, contributing to the development of life-saving medications for patients suffering from cardiovascular diseases. Its specific structural features enable the creation of targeted therapies that can help manage and treat various heart conditions more effectively.

Upstream product

• 1219915-02-2 (S)-2-chloro-1-((R)-6-fluoro-1-benzopyran-2-yl)-ethanol 
• 1315508-95-2 (1S)-2-chloro-1-[(2R)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]ethan-1-ol 
• 1219914-99-4 2-chloro-1-[(2R)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]ethan-1-one 
• 99199-61-8 C₁₂H₁₃FO₃ 
• 1345202-53-0 (2S)-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-{[(4-methylphenyl)sulfonyl]oxy}ethyl acetate 
• 1345202-52-9 (2S)-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-hydroxyethyl acetate 
• 1345202-60-9 (2S)-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-tosyloxyethyl-2,2-dimethylpropanoate 
• 1345202-57-4 (2S)-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-hydroxyethyl-2,2-dimethylpropanoate 
• 129050-26-6 (2R)-6-fluoro-2-[(2S)-oxiran-2-yl]-3,4-dihydro-2H-chromene 
• 793669-26-8 [1R*(R*)]-6-fluoro-3,4-dihydro-2-(oxiran-2-yl)-2H-chromene 
• 621-84-1 O-benzyl carbamate 
• 303176-44-5 2-(1,2-di(4-nitrophenylcarbonyloxy)-(1R)-ethyl)-6-fluoro-(2R)-3H,4H-chromene 
• 303176-36-5 ethyl 5-(2-tert-butyldimethylsilyloxy-5-fluoro-phenyl)-2-pentenoate 
• 303176-37-6 5-(2-tert-butyldimethylsilyloxy-5-fluoro-phenyl)-(E)-2-penten-1-ol 

Downstream Products

• 1029684-20-5 (R)-2-benzylamino-1-((R)-6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanol 
• 1030385-17-1 (SRRR)-d-N-benzilnebivolol 
• 118457-14-0 R 67142 
• 118457-16-2 nebivolol 
• 1199945-26-0 2-{benzyl-[2-(6-fluoro-chroman-2-yl)-2-hydroxy-ethyl]-amino}-1-(6-fluoro-chroman-2-yl)-ethanol 
• 1421916-53-1 C₂₉H₃₁F₂NO₄ 
• 118457-14-0 (+)-Nebivolol 
• 1033725-64-2 (S,R,R,R)-2-[N-benzyl-N-(2-benzyloxy-2-(6-fluorochroman-2-yl)ethyl)amino]-1-(6-fluorochroman-2-yl)ethanol 
• 152520-56-4 d-nebivolol hydrochloride 

Relevant articles and documents

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 nebivolol and wherein the intermediate compound

The invention discloses a preparation method of nebivolol used for preparing medicines for treating hypertension of slight or medium degrees, and an intermediate compound. The preparation method comprises the following steps: taking 6-fluoro-2-(1-hydroxy-2-paratoluensulfonyl oxygroup-ethyl)-3,4-dihydrobenzopyrans as an initial raw material, introducing amino, then coupling with 6- fluoro-3,4-dihydro-2-epoxy ethyl-2H-1-benzopyran, and preparing (S,R,R,R) and (R,S,S,S)-nebivolol. Compared with a prior art, the preparation method has the advantages of novel design, simple operation and high yield, the usage of hazardous reagent such as ssodium azide and sodium hydride can be avoided, a column chromatography purifying method is avoided, so that the preparation method conforms to industrial production.

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.

METHOD FOR PREPARING NEBIVOLOL

The present invention relates to a process for the preparation of nebivolol and, more particularly, to an improved process of synthesizing an alpha-haloketone of formula a key intermediate in the preparation of nebivolol.

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-

PROCESS FOR PREPARING NEBIVOLOL

The present invention relates to a process for preparing Nebivolol and, more particularly, to an improved process for synthesizing enantiomerically enriched 6-fluoro chroman alcohol or epoxide derivatives of formula, wherein R and X is defined in the description; as useful intermediates in the preparation of Nebivolol.

Sulfoxide-directed stereocontrolled access to 2H-chromans: Total synthesis of the (S,R,R,R)-enantiomer of the antihypertensive drug nebivolol

A homochiral sulfoxide-directed reductive deoxygenation of 2-(p-tolylsulfinyl)methyl-2-chromanols allows the stereoselective formation of 2H-chromans with up to 95:5 diastereoisomeric ratio. This new methodology was applied in a short and convergent enantioselective synthesis of the (S,R,R,R)-enantiomer of the antihypertensive drug Nebivolol. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

PROCESS FOR PREPARING NEBIVOLOL

The present invention relates to a process for preparing nebivolol and, more particularly, to a process for preparing d-nebivolol and its enantiomer /-nebivolol or acid addition salts thereof starting from commercially available or easily obtainable 2,2-dimethyl-l,3 dioxolane-4- carbaldehyde and a vinyl Grignard reagent.

Enantioselective total synthesis of the antihypertensive agent (S,R,R,R)-Nebivolol

The total synthesis of (S,R,R,R)-Nebivolol, a hypertensive agent, is reported. Claisen rearrangement and a one-pot Sharpless asymmetric epoxidation, intramolecular epoxide opening with internal phenoxide anion to generate the chiral chromane are the key s