rac N-Benzyl Nebivolol

Base Information

• Chemical Name: rac N-Benzyl Nebivolol
• CAS No.: 929706-85-4
• Molecular Formula: C29H31F2NO4
• Molecular Weight: 495.566
• DSSTox Substance ID: DTXSID60470220
• Mol file: 929706-85-4.mol

Synonyms:rac N-Benzyl Nebivolol;929706-85-4;racN-BenzylNebivolol-d4;2-[benzyl-[2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-hydroxyethyl]amino]-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanol;SCHEMBL2516029;SCHEMBL13762673;DTXSID60470220;STEPXTPIBUXRLE-UHFFFAOYSA-N;FT-0662842;FT-0662843;alpha,alpha'-[[(phenylmethyl)imino]bis methylene]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol];alpha,alpha'-[phenylmethyliminobis (methylene)]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol]

Chemical Property of rac N-Benzyl Nebivolol

Chemical Property:

• PSA: 62.16000
• LogP: 4.27620
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 495.22211479
• Heavy Atom Count: 36
• Complexity: 634

Purity/Quality:

98%,99%, ^*data from raw suppliers

rac N-benzyl nebivolol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C=CC(=C2)F)OC1C(CN(CC3=CC=CC=C3)CC(C4CCC5=C(O4)C=CC(=C5)F)O)O
• Uses: Protected Nebivolol.

Technology Process of rac N-Benzyl Nebivolol

There total 14 articles about rac N-Benzyl Nebivolol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran (99199-90-3,793669-26-8,876514-31-7) + benzylamine (100-46-9) → α,α'-[[(phenylmethyl)imino]bismethylene]bis-[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol] (929706-85-4)

Guidance literature:

In isopropyl alcohol; Reflux;

Reference yield: 82.0%

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran (99199-90-3,793669-26-8,876514-31-7) + 6-fluoro-3,4-dihydro-α-[[(phenylmethyl)amino]methyl]-2H-1-benzopyran-2-methanol (99199-91-4,129050-27-7) → α,α'-[[(phenylmethyl)imino]bismethylene]bis-[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol] (929706-85-4)

Guidance literature:

In ethanol; for 4h; Heating;

Reference yield:

(+/-)-2-{benzyl-[2-(6-fluoro-(2R*)-chroman-2-yl)-(2S*)-hydroxy-ethyl]-amino}-1-(6-fluoro-(2S*)-chroman-2-yl)-ethanone + (+/-)-4-benzyl-2-[6-fluoro-(2R*)-chroman-2-yl]-(6S*)-[6-fluoro-(2S*)-chroman-2-yl]-morpholin-2-ol → N-benzylnebivolol (929706-85-4) + (+/-)-[2R*[S*[R*(S*)]]]-α,α'-[[(phenylmethyl)imino]bis(methylene)]bis[6-fluoro-chroman-2-methanol] (929706-85-4)

Guidance literature:

(+/-)-2-{benzyl-[2-(6-fluoro-(2R*)-chroman-2-yl)-(2S*)-hydroxy-ethyl]-amino}-1-(6-fluoro-(2S*)-chroman-2-yl)-ethanone; (+/-)-4-benzyl-2-[6-fluoro-(2R*)-chroman-2-yl]-(6S*)-[6-fluoro-(2S*)-chroman-2-yl]-morpholin-2-ol; With lithium borohydride; Ti(OiPr)4; In tetrahydrofuran; at -15 - 5 ℃; for 2.5 - 3h;

With sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane;

upstream raw materials:

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran

6-fluoro-3,4-dihydro-α-[[(phenylmethyl)amino]methyl]-2H-1-benzopyran-2-methanol

6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde

Downstream raw materials:

(+/-)-[2R*[1S*,5S*(S*)]]-α,α-[iminobis(methylene)]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol]

α,α'-iminobis(methylene)bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol] hydrochloride

R 67142

nebivolol

Refernces

• 1、 -. "PROCESS FOR ISOLATION OF A MIXTURE OF RRRS AND SSSR CONFIGURATIONS OF NEBIVOLOL INTERMEDIATES". Page/Page column 8. . Retrieved 2010/10/19.
• 2、 Bai, Yihui,Chen, Xinzhi. "A mild synthesis of α,α′-[iminobismethylene]bis[6-fluoro- 3,4-dihydro-2H-1 -benzopyran-2-methanol]". . p. 807 - 808. Retrieved 2007/10/03.