Benzenemethanol, a-[[[2-(4-aminophenyl)ethyl]amino]methyl]-, (aR)-

Base Information

• Chemical Name: Benzenemethanol, a-[[[2-(4-aminophenyl)ethyl]amino]methyl]-, (aR)-
• CAS No.: 391901-45-4
• Molecular Formula: C16H20N2O
• Molecular Weight: 256.348
• Mol file: 391901-45-4.mol

Synonyms:(R)-2-(4-aminophenylethylamine)-1-phenylethanol;Mirabegron Impurity 6;(R)-2-[2-(4-Amino-phenyl)-ethylamino]-1-phenyl-ethanol;(1R)-2-[[2-(4-aminophenyl)ethyl]amino]-1-phenylethanol;(R)-2-((4-Aminophenethyl)amino)-1-phenylethanol;(R)-2-[[2-(4-aminophenyl)ethyl]amino]-1-phenylethanol;Mirabegron Impurity 20;(1 R)-2-[(4-aminophenethyl)amino]-1-phenyl-1-ethanol;

Chemical Property of Benzenemethanol, a-[[[2-(4-aminophenyl)ethyl]amino]methyl]-, (aR)-

Chemical Property:

• Boiling Point: 447.9±24.0 °C(Predicted)
• PKA: 13.98±0.20(Predicted)
• PSA: 58.28000
• Density: 1.137±0.06 g/cm3(Predicted)
• LogP: 3.10660
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly)

Purity/Quality:

98%, ^*data from raw suppliers

(R)-2-((4-Aminophenethyl)amino)-1-phenylethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R)-2-((4-Aminophenethyl)amino)-1-phenylethanol is an intermediate in the synthesis of Mirabegron related compounds. irabegron is a potent bladder relaxant and reagent for diabetes remedy.

Technology Process of Benzenemethanol, a-[[[2-(4-aminophenyl)ethyl]amino]methyl]-, (aR)-

There total 25 articles about Benzenemethanol, a-[[[2-(4-aminophenyl)ethyl]amino]methyl]-, (aR)- 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: 97.6%

2-(4-aminophenyl)ethyl chloride (81865-10-3) + (R)-2-Amino-1-phenylethanol (2549-14-6,1936-63-6) → YM-208876 (391901-45-4)

Guidance literature:

With triethylamine; In methanol; at 60 - 65 ℃; for 8h; Temperature;

Reference yield: 95.0%

(R)-2-(4-aminophenyl)-N-(2-hydroxy-2-phenylethyl)acetamide → YM-208876 (391901-45-4)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminum hydride; In toluene; at 25 ℃; for 48h; Inert atmosphere;

DOI:10.1021/acs.joc.7b00079

Reference yield: 91.71%

(R)-2-[[2′-(4-nitrophenyl)ethyl]amino]-1-phenylethanol hydrochloride (521284-21-9) → YM-208876 (391901-45-4)

Guidance literature:

With palladium 10% on activated carbon; ammonium formate; In methanol; at 65 ℃; for 5h; Reflux;

upstream raw materials:

p-Aminophenethylamine

(R)-Styrene oxide

(S)-styrene oxide

(R)-2-[[2′-(4-nitrophenyl)ethyl]amino]-1-phenylethanol hydrochloride

Downstream raw materials:

(R)-2-(2-aminothiazol-4-yl)-4'-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetanilide

tert-butyl 4-[(2,4-dioxo-1,3-thiazolidin-5-yl)amino]phenethyl[(2 R)-2-hydroxy-2-phenylethyl]carbamate

(R)-(4-aminophenylethyl)(2-hydroxy-2-phenylethyl)carbamic acid tert-butyl ester

Refernces

• 1、 -. "Synthesis method of (1R)-2-[[[2-(4-aminophenyl) ethyl] amino] methyl] benzyl alcohol". Paragraph 0018-0020. . Retrieved 2020/04/22.
• 2、 -. "Preparation method of mirabegron". . . Retrieved 2019/04/30.