4-(4-Bromophenyl)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-3-carboxylic acid

Base Information

• Chemical Name: 4-(4-Bromophenyl)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-3-carboxylic acid
• CAS No.: 939757-97-8
• Molecular Formula: C₁₆H₂₀BrNO₄
• Molecular Weight: 370.243
• European Community (EC) Number: 890-416-6
• DSSTox Substance ID: DTXSID00585620
• Mol file: 939757-97-8.mol

Synonyms:939757-97-8;4-(4-bromophenyl)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-3-carboxylic acid;4-(4-Bromophenyl)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid;1217829-96-3;TRANS-4-(4-BROMOPHENYL)-1-(TERT-BUTOXYCARBONYL)PYRROLIDINE-3-CARBOXYLIC ACID;trans-4-(4-Bromophenyl)-1-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid;SCHEMBL7890064;DTXSID00585620;AKOS015841216;PB35482;SB10326;(3R,4S)-4-(4-bromophenyl)-1-[(tert-;butoxy)carbonyl]pyrrolidine-3-carboxylic acid;EN300-1454188;A844759;1-Boc-4-(4-bromo-phenyl)-pyrrolidine-3-carboxylic acid;4-(4-Bromophenyl)-1-(tert-butoxycarbonyl)-3-pyrrolidinecarboxylic acid;4-(4-bromophenyl)-1-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid;4-(4-bromophenyl)-1-[(2-methylpropan-2-yl)oxy-oxomethyl]-3-pyrrolidinecarboxylic acid

Chemical Property of 4-(4-Bromophenyl)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 5.77E-10mmHg at 25°C
• Boiling Point: 478.5°C at 760 mmHg
• Flash Point: 243.2°C
• PSA: 66.84000
• Density: 1.426g/cm³
• LogP: 3.42210
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 369.05757
• Heavy Atom Count: 22
• Complexity: 426

Purity/Quality:

97% ^*data from raw suppliers

4-(4-Bromophenyl)-1-(tert-butoxycarbonyl)-3-pyrrolidinecarboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(C(C1)C(=O)O)C2=CC=C(C=C2)Br

Technology Process of 4-(4-Bromophenyl)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-3-carboxylic acid

There total 4 articles about 4-(4-Bromophenyl)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-3-carboxylic acid 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: 50.0%

rac-(trans-3,4)-4-(4-bromophenyl)pyrrolidine-3-carboxylic acid ethyl ester + di-tert-butyl dicarbonate (24424-99-5) → rac-(trans-3,4)-4-(4-bromophenyl)pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (1217829-96-3,939757-97-8)

Guidance literature:

rac-(trans-3,4)-4-(4-bromophenyl)pyrrolidine-3-carboxylic acid ethyl ester; With sodium hydroxide; In acetonitrile; at 20 ℃; for 2h;

di-tert-butyl dicarbonate; With sodium carbonate; In acetonitrile; at 20 ℃;

Reference yield:

rac-(trans-3,4)-1-benzyl-4-(4-bromophenyl)pyrrolidine-3-carboxylic acid ethyl ester → rac-(trans-3,4)-4-(4-bromophenyl)pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (1217829-96-3,939757-97-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / acetonitrile / 3 h / 60 °C

2.1: acetic acid; zinc / 3 h / 20 °C / Inert atmosphere

3.1: sodium hydroxide / acetonitrile / 2 h / 20 °C

3.2: 16 h / 20 °C

With potassium carbonate; acetic acid; sodium hydroxide; zinc; In acetonitrile;

DOI:10.1021/jm3011838

Reference yield:

rac-(trans-3,4)-4-(4-bromophenyl)pyrrolidine-1,3-dicarboxylic acid 3-ethyl ester 1-(2,2,2-trichloroethyl)ester → rac-(trans-3,4)-4-(4-bromophenyl)pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (1217829-96-3,939757-97-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid; zinc / 3 h / 20 °C / Inert atmosphere

2.1: sodium hydroxide / acetonitrile / 2 h / 20 °C

2.2: 16 h / 20 °C

With acetic acid; sodium hydroxide; zinc; In acetonitrile;

DOI:10.1021/jm3011838

upstream raw materials:

di-tert-butyl dicarbonate

ethyl (E)-3-(4-bromophenyl)-2-propenoate

Refernces

• 1、 -. "ORTHO AMINOAMIDES FOR THE TREATMENT OF CANCER". Page/Page column 68. . Retrieved 2010/09/05.