Pyrrolidine-2,3-dicarboxylic acid

Base Information

• Chemical Name: Pyrrolidine-2,3-dicarboxylic acid
• CAS No.: 147235-95-8
• Molecular Formula: C₆H₉NO₄
• Molecular Weight: 159.142
• DSSTox Substance ID: DTXSID30933074
• Mol file: 147235-95-8.mol

Synonyms:2,3-PDCA;2,3-pyrrolidinedicarboxylic acid;L-trans-2,3-pyrrolidine dicarboxylate;pyrrolidine-2,3-dicarboxylic acid

Chemical Property of Pyrrolidine-2,3-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 3.05E-08mmHg at 25°C
• Boiling Point: 420.3°Cat760mmHg
• Flash Point: 208°C
• PSA: 86.63000
• Density: 1.456g/cm³
• LogP: -0.53750
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 159.05315777
• Heavy Atom Count: 11
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC(C1C(=O)O)C(=O)O

Technology Process of Pyrrolidine-2,3-dicarboxylic acid

There total 33 articles about Pyrrolidine-2,3-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:

(2S,3R)-Pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester → (+/-)-Pyrrolidine-2,3-dicarboxylic acid (131669-74-4,147235-95-8,147332-07-8,147332-08-9,147332-09-0,147332-10-3)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; for 12h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(97)00238-4

Reference yield:

(1R,5S)-7,7-Dichloro-6-oxo-2-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester → (+/-)-Pyrrolidine-2,3-dicarboxylic acid (131669-74-4,147235-95-8,147332-07-8,147332-08-9,147332-09-0,147332-10-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Me₂CuLi / tetrahydrofuran / -50 deg C, 50 min; -50 deg C -> r.t., 3 h

2: 1.) O₃; 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C; 2.) -78 deg C -> r.t., 12 h

3: H₂ / Pd(OH)2 / methanol / 12 h / Ambient temperature

With dimethylsulfide; lithium dimethylcuprate; hydrogen; ozone; palladium dihydroxide; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(97)00238-4

Reference yield:

(1R,5S)-7,7-Dichloro-6-oxo-2-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester → (+/-)-Pyrrolidine-2,3-dicarboxylic acid (131669-74-4,147235-95-8,147332-07-8,147332-08-9,147332-09-0,147332-10-3)

Guidance literature:

Multi-step reaction with 5 steps

1: Me₂CuLi / tetrahydrofuran / -50 deg C, 50 min; -50 deg C -> r.t., 3 h

2: 1.) O₃; 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C; 2.) -78 deg C -> r.t., 12 h

3: methanol; diethyl ether / 0.25 h / 0 °C

4: H₂ / Pd(OH)2 / methanol / 12 h / Ambient temperature

5: 6M HCl, Dowex 50-X₈ / 12 h / 70 °C

With hydrogenchloride; dimethylsulfide; Dowex 50-X₈; lithium dimethylcuprate; hydrogen; ozone; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1016/S0040-4039(97)00238-4

upstream raw materials:

Methyl N-pivaloylprolinate

2-<1-(2,2-dimethylpropanoyl)pyrrolidin-2-ylidene>-1,3-dithiane

2-<3-(Methoxycarbonyl)-N-pivaloylpyrrolidin-2-ylidene>-1,3-dithiane

2-(4-azidobut-1-ylidene)-1,3-dithiane

Refernces

• 1、 Moss, William O.,Jones, Annette C.,Wisedale, Richard,Mahon, Mary F.,Molloy, Kieran C.,et al.. "2-Amino Ketene S,S-Acetals as α-Amino Acid Homoenolate Equivalents. Synthesis of 3-Substituted Prolines and Molecular Structure of 2-(N-Pivaloylpyrrolidin-2-ylidene)-1,3-dithiane". . p. 2615 - 2624. Retrieved 2007/10/02.