(1R)-1-[3-Amino-4-(benzyloxy)phenyl]-2-[benzyl[(alphaR)-alpha-methyl-4-methoxyphenethyl]amino]ethanol

Base Information

• Chemical Name: (1R)-1-[3-Amino-4-(benzyloxy)phenyl]-2-[benzyl[(alphaR)-alpha-methyl-4-methoxyphenethyl]amino]ethanol
• CAS No.: 289657-26-7
• Molecular Formula: C₃₂H₃₆N₂O₃
• Molecular Weight: 496.649
• UNII: F6X7R9XU3J
• Nikkaji Number: J1.629.044K
• Mol file: 289657-26-7.mol

Synonyms:F6X7R9XU3J;SCHEMBL719264;TVLLMHMSGGBZNO-XJFCNFDWSA-N;(1R)-1-[3-Amino-4-(benzyloxy)phenyl]-2-[benzyl[(alphaR)-alpha-methyl-4-methoxyphenethyl]amino]ethanol;(alphaR)-3-Amino-alpha-[[[(1R)-2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]methyl]-4-(phenylmethoxy)benzenemethanol;(R)-1-(3-Amino-4-(benzyloxy)phenyl)-2-(benzyl((R)-1-(4-methoxyphenyl)propan-2-yl)amino)ethanol;(R,R)-3-amino-alpha-[[[2-(4-methoxyphenyl)-1-methylethyl](phenyl methyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol;289657-26-7;Benzenemethanol, 3-amino-alpha-[[[(1R)-2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]methyl]-4-(phenylmethoxy)-, (alphaR)-

Chemical Property of (1R)-1-[3-Amino-4-(benzyloxy)phenyl]-2-[benzyl[(alphaR)-alpha-methyl-4-methoxyphenethyl]amino]ethanol

Chemical Property:

• XLogP3: 5.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 496.27259301
• Heavy Atom Count: 37
• Complexity: 613

Purity/Quality:

98% HPLC ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CC1=CC=C(C=C1)OC)N(CC2=CC=CC=C2)CC(C3=CC(=C(C=C3)OCC4=CC=CC=C4)N)O
• Isomeric SMILES: C[C@H](CC1=CC=C(C=C1)OC)N(CC2=CC=CC=C2)C[C@@H](C3=CC(=C(C=C3)OCC4=CC=CC=C4)N)O

Technology Process of (1R)-1-[3-Amino-4-(benzyloxy)phenyl]-2-[benzyl[(alphaR)-alpha-methyl-4-methoxyphenethyl]amino]ethanol

There total 13 articles about (1R)-1-[3-Amino-4-(benzyloxy)phenyl]-2-[benzyl[(alphaR)-alpha-methyl-4-methoxyphenethyl]amino]ethanol 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: 84.21%

(R,R)-3-nitro-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol (245759-65-3) → (R,R)-3-amino-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenyl methyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol (289657-26-7)

Guidance literature:

(R,R)-3-nitro-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol; With ammonium formate; palladium 10% on activated carbon; In N,N-dimethyl-formamide; at 40 - 75 ℃; for 2h;

With ammonia; In water; Product distribution / selectivity;

Reference yield:

(R)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol (188690-82-6) → (R,R)-3-amino-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenyl methyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol (289657-26-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / aqueous sodium hydroxide / methanol / 0.5 h

2: 90 °C

3: H₂ / PtO₂

With sodium hydroxide; hydrogen; platinum(IV) oxide; In methanol;

DOI:10.1016/S0040-4039(97)00088-9

Reference yield:

4-benzyloxy-3-nitrophenacyl bromide (43229-01-2) → (R,R)-3-amino-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenyl methyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol (289657-26-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / oxazaborolidine from cis (1R,2S)-aminoindanol and trimethylboroxine, BH₃ / tetrahydrofuran / -15 °C

2: 98 percent / aqueous sodium hydroxide / methanol / 0.5 h

3: 90 °C

4: H₂ / PtO₂

With sodium hydroxide; oxazaborolidine from cis (1R,2S)-aminoindanol and trimethylboroxine; borane; hydrogen; platinum(IV) oxide; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(97)00088-9

upstream raw materials:

(R,R)-3-nitro-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol

4-methoxybenzyl methyl ketone

4-benzyloxy-3-nitrophenacyl bromide

(R)-(-)-1-(4'-methoxyphenyl)-2-benzylaminopropane

Downstream raw materials:

(R,R)-formoterol

N-[5-[(1R)-Hydroxy-2-[[(1R)-methyl-2-(4-methoxyphenyl)ethyl](phenylmethyl)amino]ethyl]-2-(phenylmethoxy)phenyl]-formamide

Refernces

• 1、 -. "PROCESSES FOR PREPARING SUBSTANTIALLY PURE ARFORMOTEROL AND ITS INTERMEDIATES". Page/Page column 13. . Retrieved 2012/01/13.
• 2、 Hett, Robert,Fang, Qun Kevin,Gao, Yun,Hong, Yaping,Butler, Hal T.,Nie, Xiaoyi,Wald, Stephen A.. "Enantio- and diastereoselective synthesis of all four stereoisomers of formoterol". . p. 1125 - 1128. Retrieved 2007/10/03.