4-(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-[(S)-hydroxy(2-methoxyphenyl)methyl]phenoxy)-2-methylbutan-2-ol

Base Information

• Chemical Name: 4-(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-[(S)-hydroxy(2-methoxyphenyl)methyl]phenoxy)-2-methylbutan-2-ol
• CAS No.: 922163-04-0
• Molecular Formula: C₂₄H₃₄ClNO₄
• Molecular Weight: 435.991

Synonyms:4-(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-[(S)-hydroxy(2-methoxyphenyl)methyl]phenoxy)-2-methylbutan-2-ol

Chemical Property of 4-(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-[(S)-hydroxy(2-methoxyphenyl)methyl]phenoxy)-2-methylbutan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-[(S)-hydroxy(2-methoxyphenyl)methyl]phenoxy)-2-methylbutan-2-ol

There total 9 articles about 4-(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-[(S)-hydroxy(2-methoxyphenyl)methyl]phenoxy)-2-methylbutan-2-ol 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:

4-(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-[hydroxy(2-methoxyphenyl)methyl]phenoxy)-2-methylbutan-2-ol (922163-03-9) → 4-(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-[(S)-hydroxy(2-methoxyphenyl)methyl]phenoxy)-2-methylbutan-2-ol (922163-04-0) + 4-(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-[(R)-hydroxy(2-methoxyphenyl)methyl]phenoxy)-2-methylbutan-2-ol

Guidance literature:

With Chiralcel OD column; In hexane; isopropyl alcohol; at 20 ℃; Resolution of racemate; HPLC conditions;

DOI:10.1016/j.bmc.2011.07.007

Reference yield:

3-methyl-butane-1,3-diol (2568-33-4) → 4-(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-[(S)-hydroxy(2-methoxyphenyl)methyl]phenoxy)-2-methylbutan-2-ol (922163-04-0) + 4-(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-[(R)-hydroxy(2-methoxyphenyl)methyl]phenoxy)-2-methylbutan-2-ol

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 7.5 h / 20 °C / Cooling with ice

2.1: sodium carbonate / N,N-dimethyl-formamide / 6 h / 60 °C

3.1: sec.-butyllithium / tetrahydrofuran; hexane; cyclohexane / 0.5 h / -78 - 20 °C

3.2: 1.5 h / -78 - -50 °C

4.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 4 h / 0 - 50 °C

4.2: 0.08 h

5.1: Chiralcel OD column / hexane; isopropyl alcohol / 20 °C / Resolution of racemate; HPLC conditions

With sec.-butyllithium; sodium carbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1016/j.bmc.2011.07.007

Reference yield:

3-hydroxy-3-methylbutyl methanesulfonate (135859-47-1) → 4-(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-[(S)-hydroxy(2-methoxyphenyl)methyl]phenoxy)-2-methylbutan-2-ol (922163-04-0) + 4-(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-[(R)-hydroxy(2-methoxyphenyl)methyl]phenoxy)-2-methylbutan-2-ol

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium carbonate / N,N-dimethyl-formamide / 6 h / 60 °C

2.1: sec.-butyllithium / tetrahydrofuran; hexane; cyclohexane / 0.5 h / -78 - 20 °C

2.2: 1.5 h / -78 - -50 °C

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 4 h / 0 - 50 °C

3.2: 0.08 h

4.1: Chiralcel OD column / hexane; isopropyl alcohol / 20 °C / Resolution of racemate; HPLC conditions

With sec.-butyllithium; sodium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; cyclohexane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1016/j.bmc.2011.07.007

upstream raw materials:

3-methyl-butane-1,3-diol

3-hydroxy-3-methylbutyl methanesulfonate

N-[4-chloro-2-(3-hydroxy-3-methylbutoxy)phenyl]-2,2-dimethylpropanamide

N-(4-chloro-2-[hydroxy(2-methoxyphenyl)methyl]-6-(3-hydroxy-3-methylbutoxy)phenyl)-2,2-dimethylpropanamide

Downstream raw materials:

4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)-methyl]-6-(3-hydroxy-3-methylbutoxy)phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoic acid

ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-(3-hydroxy-3-methylbutoxy)phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate

(3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-(3-hydroxy-3-methylbutoxy)phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylic acid

methyl 4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)-methyl]-6-(3-hydroxy-3-methylbutoxy)phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoate

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