Diethyl Pyrrolidine-2,4-dicarboxylate

Base Information

• Chemical Name: Diethyl Pyrrolidine-2,4-dicarboxylate
• CAS No.: 79265-57-9
• Molecular Formula: C₁₀H₁₇NO₄
• Molecular Weight: 215.249
• DSSTox Substance ID: DTXSID90403561
• Mol file: 79265-57-9.mol

Synonyms:Diethyl Pyrrolidine-2,4-dicarboxylate;79265-57-9;DIETHYL 2,4-PYRROLIDINEDICARBOXYLATE;DTXSID90403561;AG-H-18044

Chemical Property of Diethyl Pyrrolidine-2,4-dicarboxylate

Chemical Property:

• Vapor Pressure: 0.00183mmHg at 25°C
• Refractive Index: 1.461
• Boiling Point: 292.4°C at 760 mmHg
• Flash Point: 130.7°C
• PSA: 64.63000
• Density: 1.115g/cm³
• LogP: 0.41950
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 215.11575802
• Heavy Atom Count: 15
• Complexity: 242

Purity/Quality:

97% ^*data from raw suppliers

DIETHYL-2,4-PYRROLIDINEDICARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CC(NC1)C(=O)OCC

Technology Process of Diethyl Pyrrolidine-2,4-dicarboxylate

There total 12 articles about Diethyl Pyrrolidine-2,4-dicarboxylate 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: 85.0%

3,5-dicarbethoxy-Δ2-pyrroline (79265-56-8) → Pyrrolidine-2,4-dicarboxylic acid diethyl ester (79265-57-9)

Guidance literature:

With sodium tetrahydroborate; In methanol;

DOI:10.1016/S0040-4039(01)90536-2

Reference yield:

(5S,7S)-8a-Methyl-octahydro-furo[2,3-d]pyrrolo[2,1-b]thiazole-5,7-dicarboxylic acid diethyl ester (79265-55-7) → diethyl 2,4-pyrrolidine dicarboxylate (79265-57-9,103871-58-5,103871-66-5)

Guidance literature:

With hydrogenchloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; Yield given. Multistep reaction; 1) benzene, reflux, 3 h, 2) EtOH-benzene, r.t., 3 h;

DOI:10.1016/S0040-4020(01)96707-9

Reference yield:

3-Ethoxycarbonylmethyl-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium; bromide (103871-46-1) → diethyl 2,4-pyrrolidine dicarboxylate (79265-57-9,103871-58-5,103871-66-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) Et₃N, 2) silica gel / 1) acetonitrile, 0 deg C, 3 h (further solvent, thiazolium salts, and olefins); 2) EtoAc-hexane

2: 67 percent / AgNO₃, NaHCO₃ / H₂O / 1 h

With silica gel; sodium hydrogencarbonate; silver nitrate; triethylamine; In water;

DOI:10.1016/S0040-4020(01)96707-9

upstream raw materials:

3,5-dicarbethoxy-Δ²-pyrroline

1H-pyrrole-2,4-dicarboxylic acid diethyl ester

C₁₀H₁₅NO₃S

8a-Methyl-octahydro-furo[2,3-d]pyrrolo[2,1-b]thiazole-5,7-dicarboxylic acid diethyl ester

Refernces

• 1、 Kraus, George A.,Nagy, Jon O.. "A CONVERGENT SYNTHESIS OF SUBSTITUTED PYRROLIDINES BY 1,3 DIPOLAR CYCLOADDITION". . p. 2727 - 2730. Retrieved 2007/10/02.