(R)-Metoprolol

Base Information

• Chemical Name: (R)-Metoprolol
• CAS No.: 81024-43-3
• Deprecated CAS: 91324-77-5
• Molecular Formula: C15H25 N O3
• Molecular Weight: 267.368
• DSSTox Substance ID: DTXSID20230862
• Nikkaji Number: J239.291G
• Wikidata: Q83111604
• ChEMBL ID: CHEMBL1741004
• Mol file: 81024-43-3.mol

Synonyms:(R)-Metoprolol;81024-43-3;(R)-(+)-Metoprolol;(+)-Metoprolol;(2R)-1-[4-(2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol;(2R)-1-[4-(2-methoxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol;2-Propanol, 1-(4-(2-methoxyethyl)phenoxy)-3-((1-methylethyl)amino)-, (2R)-;r-metoprolol;d-Metoprolol;SCHEMBL40918;BIDD:GT0581;CHEMBL1741004;BDBM81884;DTXSID20230862;STR11440;AKOS030242833;CS-T-58832;NCGC00021148-01;EN300-25893794;(R)-1-(Isopropylamino)-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol;(2R)-1-[4-(2-Methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]-2-propanol

Chemical Property of (R)-Metoprolol

Chemical Property:

• Vapor Pressure: 4.52E-07mmHg at 25°C
• Melting Point: 39-42°C
• Boiling Point: 398.6°C at 760 mmHg
• Flash Point: 194.9°C
• PSA: 50.72000
• Density: 1.033g/cm³
• LogP: 2.00410
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 267.18344366
• Heavy Atom Count: 19
• Complexity: 215

Purity/Quality:

95-99% ^*data from raw suppliers

(R)-Metoprolol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=C(C=C1)CCOC)O
• Isomeric SMILES: CC(C)NC[C@H](COC1=CC=C(C=C1)CCOC)O
• Uses: (R)-Enantiomer of Metoprolol. Antihypertensive; antianginal; antiarrhythmic (class II). (R)-Enantiomer of Metoprolol. Antihypertensive; antianginal; antiarrhythmic (class II)

Technology Process of (R)-Metoprolol

There total 6 articles about (R)-Metoprolol 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: 85.0%

isopropylamine (75-31-0) + (2S)-2-{[4-(2-Methoxyethyl)phenoxy]methyl}oxirane (105780-38-9) → (2R)-metoprolol (81024-43-3,37350-58-6) + S-(-)-metoprolol (81024-42-2,37350-58-6)

Guidance literature:

With zinc(II) bis(tetrafluoroborate) hydrate; at 20 ℃; for 2h; optical yield given as %ee; Inert atmosphere; Neat (no solvent);

DOI:10.1021/jo201473f

Reference yield: 83.0%

isopropylamine (75-31-0) + (R)-2-{[4-(2-methoxyethyl)phenoxy]methyl}oxirane (133397-54-3) → (2R)-metoprolol (81024-43-3,37350-58-6) + S-(-)-metoprolol (81024-42-2,37350-58-6)

Guidance literature:

With zinc(II) bis(tetrafluoroborate) hydrate; at 20 ℃; for 2h; optical yield given as %ee; Inert atmosphere; Neat (no solvent);

DOI:10.1021/jo201473f

Reference yield:

(RS)-metoprolol (51384-51-1,37350-58-6) → (2R)-metoprolol (81024-43-3,37350-58-6) + S-(-)-metoprolol (81024-42-2,37350-58-6)

Guidance literature:

With MCCD-HPS packed column; In hydrogenchloride; acetonitrile; pH=8.6;

DOI:10.1021/ac0204909

upstream raw materials:

isopropylamine

2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane

(RS)-metoprolol

4-(2-methoxyethyl)phenol

Downstream raw materials:

(+)-O-Demethylmetoprolol

(1'S,2R)-3-<4-(1-hydroxy-2-methyloxyethyl)phenoxy>-1-(isopropylamino)-2-propanol

(1'R,2R)-3-<4-(1-hydroxy-2-methyloxyethyl)phenoxy>-1-(isopropylamino)-2-propanol

Refernces

• 1、 Li, Jiaxi,Liu, Ruixia,Wang, Liyang,Liu, Xiaoling,Gao, Hongjie. "Enantioseparation of chiral pharmaceuticals by vancomycin-bonded stationary phase and analysis of chiral recognition mechanism". . p. 236 - 247. Retrieved 2019/02/01.
• 2、 Xu, Shujuan,Wang, Yuying,Tang, Yixia,Ji, Yibing. "A protein-based mixed selector chiral monolithic stationary phase in capillary electrochromatography". supporting information. p. 13520 - 13528. Retrieved 2018/08/21.