Ethyl (S)-(-)-1-Ethyl-2-pyrrolidinecarboxylate

Base Information

• Chemical Name: Ethyl (S)-(-)-1-Ethyl-2-pyrrolidinecarboxylate
• CAS No.: 938-54-5
• Molecular Formula: C9H17NO2
• Molecular Weight: 171.239
• Hs Code.: 2933990090
• European Community (EC) Number: 679-973-4
• DSSTox Substance ID: DTXSID50449162
• Nikkaji Number: J534.086A
• Wikidata: Q76416273
• Mol file: 938-54-5.mol

Synonyms:938-54-5;Ethyl (S)-(-)-1-Ethyl-2-pyrrolidinecarboxylate;ethyl (2S)-1-ethylpyrrolidine-2-carboxylate;(S)-(-)-1-Ethyl-2-pyrrolidinecarboxylic Acid Ethyl Ester;L-Proline, 1-ethyl-,ethyl ester;Et-Pro-OEt;(-)-1-Ethyl-L-proline Ethyl Ester;SCHEMBL1704641;DTXSID50449162;CUDOPASYFARLIF-QMMMGPOBSA-N;MFCD00191434;(S)-(-)-1-Ethylproline ethyl ester;AKOS006238122;AKOS015838666;AS-69057;(S)-ethyl 1-ethylpyrrolidine-2-carboxylate;E0450;T73086;Ethyl (-)-(S)-1-ethyl-2-pyrrolidinecarboxylate;(S)-1-ethyl-2-pyrrolidinecarboxylic acid ethyl ester;[2S,(?)]-1-Ethyl-2-pyrrolidinecarboxylic acid ethyl ester;(S)-(-)-1-ETHYL-2-PYRROLIDINECARBOXYLICACIDETHYLESTER

Chemical Property of Ethyl (S)-(-)-1-Ethyl-2-pyrrolidinecarboxylate

Chemical Property:

• Vapor Pressure: 0.204mmHg at 25°C
• Refractive Index: -94 ° (C=0.6, CHCl3)
• Boiling Point: 209.367 °C at 760 mmHg
• Flash Point: 73.033 °C
• PSA: 29.54000
• Density: 0.999 g/cm³
• LogP: 0.97170
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 171.125928785
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl1-ethylprolinate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1CCCC1C(=O)OCC
• Isomeric SMILES: CCN1CCC[C@H]1C(=O)OCC

Technology Process of Ethyl (S)-(-)-1-Ethyl-2-pyrrolidinecarboxylate

There total 9 articles about Ethyl (S)-(-)-1-Ethyl-2-pyrrolidinecarboxylate 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: 90.0%

(S)-ethyl 1-acetylpyrrolidine-2-carboxylate (23037-82-3) → 1-ethyl-pyrrolidine-2-carboxylic acid ethyl ester (938-54-5,381670-33-3)

Guidance literature:

With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 1,3-bis-(diphenylphosphino)propane; phenylsilane; In tetrahydrofuran; at 20 - 45 ℃; Reagent/catalyst; chemoselective reaction; Catalytic behavior; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201503584

Reference yield: 71.0%

ethyl iodide (75-03-6) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → 1-ethyl-pyrrolidine-2-carboxylic acid ethyl ester (938-54-5,381670-33-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 3h; Ambient temperature;

Reference yield: 62.0%

ethyl iodide (75-03-6) + ethyl (2S)-pyrrolidine-2-carboxylate (5817-26-5) → 1-ethyl-pyrrolidine-2-carboxylic acid ethyl ester (938-54-5,381670-33-3)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 6h;

DOI:10.1021/ja0675144

upstream raw materials:

1-ethylpyrrolidine-2-carboxylic acid

diethyl 2-bromo-2-(3-bromopropyl)malonate

1-ethyl-pyrrolidine-2,2-dicarboxylic acid diethyl ester

ethyl iodide

Downstream raw materials:

(-)-(S)-1-ethyl-2-pyrrolidinecarboxamide

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

(S)-1-Ethyl-pyrrolidine-2-carboxylic acid methylamide

(S)-1-Ethyl-pyrrolidine-2-carboxylic acid dimethylamide

Refernces

• 1、 Kessar, Satinder V.,Singh, Paramjit,Singh, Kamal Nain,Venugopalan,Kaur, Amarjit,Bharatam, Prasad V.,Sharma, Arvind K.. "An experimental and computational study of stereoselectivity and reactivity in Lewis acid promoted lithiation-substitution of tertiary amines". . p. 4506 - 4507. Retrieved 2007/10/03.
• 2、 Hoegberg, Thomas,Raemsby, Sten,Stroem, Peter. "Efficient Stereoconservative Syntheses of 1-Substituted (S)- and (R)-2-Aminomethylpyrrolidines". . p. 660 - 664. Retrieved 2007/10/02.