(2R,5R)-Pyrrolidine-2,5-dicarboxylic acid

Base Information

• Chemical Name: (2R,5R)-Pyrrolidine-2,5-dicarboxylic acid
• CAS No.: 93713-35-0
• Molecular Formula: C₆H₉NO₄
• Molecular Weight: 159.142
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50437423
• Wikidata: Q72505160
• Mol file: 93713-35-0.mol

Synonyms:93713-35-0;(2R,5R)-Pyrrolidine-2,5-dicarboxylic acid;2,5-Pyrrolidinedicarboxylicacid,(2R-trans)-(9CI);SCHEMBL16620358;DTXSID50437423;AMY13833;AKOS000278474

Chemical Property of (2R,5R)-Pyrrolidine-2,5-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.535
• Boiling Point: 420.296 °C at 760 mmHg
• Flash Point: 207.988 °C
• PSA: 86.63000
• Density: 1.457 g/cm³
• LogP: -0.39500
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 159.05315777
• Heavy Atom Count: 11
• Complexity: 171

Purity/Quality:

99% ^*data from raw suppliers

(2R,5R)-2,5-PYRROLIDINEDICARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(NC1C(=O)O)C(=O)O
• Isomeric SMILES: C1C[C@@H](N[C@H]1C(=O)O)C(=O)O

Technology Process of (2R,5R)-Pyrrolidine-2,5-dicarboxylic acid

There total 12 articles about (2R,5R)-Pyrrolidine-2,5-dicarboxylic 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: 88.0%

dimethyl pyrrolidine-2,5-dicarboxylate (90088-52-1,111071-93-3,115413-67-7,116836-62-5,116836-63-6) → acido pirrolidin-2,5-dicarbossilico (35634-41-4,49653-02-3,72000-65-8,81702-31-0,93713-35-0,97275-65-5,97275-67-7)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 24h;

DOI:10.1016/j.bmcl.2012.06.074

Reference yield: 74.0%

(2R,5R)-2,5-Bis(methoxycarbonyl)pyrrolidine (115413-67-7) → (2R,5R)-2,5-Pyrrolidinedicarboxylic acid (93713-35-0)

Guidance literature:

With water; for 15h; Heating;

DOI:10.1055/s-1993-25852

Reference yield:

dimethyl (2R,5S)-2,5-dibromohexanedioate (868-72-4,53490-47-4,124819-17-6) → acido pirrolidin-2,5-dicarbossilico (35634-41-4,49653-02-3,72000-65-8,81702-31-0,93713-35-0,97275-65-5,97275-67-7)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / water; toluene / 24 h / Reflux

2: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 15201 Torr

3: sodium hydroxide / methanol / 24 h / 20 °C

With palladium 10% on activated carbon; hydrogen; potassium carbonate; sodium hydroxide; In methanol; water; toluene;

DOI:10.1016/j.bmcl.2012.06.074

upstream raw materials:

dimethyl (2R,5S)-2,5-dibromohexanedioate

dimethyl pyrrolidine-2,5-dicarboxylate

1-Benzyl-2,5-pyrrolidindicarbonsaeure-dimethylester

(2R,5R)-1-Benzyl-pyrrolidine-2,5-dicarboxylic acid

Downstream raw materials:

acido 2-fenil-2,3,5,6,7,7a-esaidro-1-oxo-3-tioxo-1H-pirrolo<1,2-c>imidazolo-5-carbossilico

Refernces

• 1、 Yamamoto,Hoshino,Fujimoto,Ohmoto,Sawada. "A convenient synthesis of enantiomeric pairs of 2,5-disubstituted pyrrolidines of C2-symmetry". . p. 298 - 302. Retrieved 2007/10/02.