1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)[2-[(Methoxycarbonyl)aMino]ethoxy]Methyl]-, 1,1-diMethylethyl ester, (3R)-

Base Information

• Chemical Name: 1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)[2-[(Methoxycarbonyl)aMino]ethoxy]Methyl]-, 1,1-diMethylethyl ester, (3R)-
• CAS No.: 942142-79-2
• Molecular Formula: C21H31ClN2O5
• Molecular Weight: 426.941
• Mol file: 942142-79-2.mol

Synonyms:1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)[2-[(Methoxycarbonyl)aMino]ethoxy]Methyl]-, 1,1-diMethylethyl ester, (3R)-

Chemical Property of 1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)[2-[(Methoxycarbonyl)aMino]ethoxy]Methyl]-, 1,1-diMethylethyl ester, (3R)-

Chemical Property:

• Vapor Pressure: 3.74E-11mmHg at 25°C
• Boiling Point: 526°C at 760 mmHg
• Flash Point: 271.9°C
• PSA: 80.59000
• Density: 1.184g/cm³
• LogP: 4.54310

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)[2-[(Methoxycarbonyl)aMino]ethoxy]Methyl]-, 1,1-diMethylethyl ester, (3R)-

There total 10 articles about 1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)[2-[(Methoxycarbonyl)aMino]ethoxy]Methyl]-, 1,1-diMethylethyl ester, (3R)- 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:

(R)-tert-butyl 3-((R)-(2-aminoethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate (942142-78-1) + methyl chloroformate (79-22-1) → (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-(methoxycarbonylamino)ethoxy)methyl)piperidine-1-carboxylate (942142-79-2)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1016/j.bmcl.2009.11.066

Reference yield:

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-ethoxy-2-oxoethoxy)methyl)piperidine-1-carboxylate (942142-76-9) → (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-(methoxycarbonylamino)ethoxy)methyl)piperidine-1-carboxylate (942142-79-2)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium tetrahydroborate / methanol / 20 °C

2: triethylamine / dichloromethane / 3 h / -5 - 20 °C

3: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C

4: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C

5: dmap; triethylamine / dichloromethane / 0 - 5 °C

With dmap; sodium tetrahydroborate; sodium azide; water; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ml200137x

Reference yield:

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate (942142-74-7) → (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-(methoxycarbonylamino)ethoxy)methyl)piperidine-1-carboxylate (942142-79-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C

1.2: 0 - 20 °C

2.1: sodium tetrahydroborate / methanol / 20 °C

3.1: triethylamine / dichloromethane / 3 h / -5 - 20 °C

4.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C

5.1: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C

6.1: dmap; triethylamine / dichloromethane / 0 - 5 °C

With dmap; sodium tetrahydroborate; sodium azide; water; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/ml200137x

upstream raw materials:

(R)-tert-butyl 3-((R)-(2-aminoethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate

methyl chloroformate

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate

(R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

Downstream raw materials:

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-1-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

methyl (2-((R)-(3-chlorophenyl)((R)-1-(((S)-1-(methylamino)-3-((S)-tetrahydro-2H-pyran-3-yl)propan-2-yl)carbamoyl)piperidin-3-yl)methoxy)ethyl)carbamate trifluoroacetate

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

(R)-tert-butyl 3-((R)-(phenyl)(2-(methoxycarbonylamino)ethoxy)methyl)piperidine-1-carboxylate

Refernces

• 1、 Xu, Zhenrong,Cacatian, Salvacion,Yuan, Jing,Simpson, Robert D.,Jia, Lanqi,Zhao, Wei,Tice, Colin M.,Flaherty, Patrick T.,Guo, Joan,Ishchenko, Alexey,Singh, Suresh B.,Wu, Zhongren,McKeever, Brian M.,Scott, Boyd B.,Bukhtiyarov, Yuri,Berbaum, Jennifer,Mason, Jennifer,Panemangalore, Reshma,Cappiello, Maria Grazia,Bentley, Ross,Doe, Christopher P.,Harrison, Richard K.,McGeehan, Gerard M.,Dillard, Lawrence W.,Baldwin, John J.,Claremon, David A.. "Optimization of orally bioavailable alkyl amine renin inhibitors". scheme or table. p. 694 - 699. Retrieved 2010/06/16.
• 2、 -. "ASPARTIC PROTEASE INHIBITORS". Page/Page column 136. . Retrieved 2010/11/27.