(S)-1-tert-Butyl 2-ethyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate

Base Information

• Chemical Name: (S)-1-tert-Butyl 2-ethyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate
• CAS No.: 178172-26-4
• Molecular Formula: C12H19NO4
• Molecular Weight: 241.287
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID60441793
• Nikkaji Number: J741.573G
• Wikidata: Q72449164
• Mol file: 178172-26-4.mol

Synonyms:178172-26-4;(S)-1-tert-Butyl 2-ethyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate;ETHYL N-BOC-L-PROLINE-4-ENE;(S)-1-Boc-2,3-dihydro-2-pyrrolecarboxylic acid ethyl ester;1-O-tert-butyl 2-O-ethyl (2S)-2,3-dihydropyrrole-1,2-dicarboxylate;(S)-2,3-Dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester;(S)-1-tert-butyl 2-ethyl 2,3-dihydropyrrole-1,2-dicarboxylate;(S)-2,3-Dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester;Ethyl N-Boc-L-prolin-4-ene;SCHEMBL1571674;1-tert-butyl 2-ethyl (2S)-2,3-dihydro-1H-pyrrole-1,2-dicarboxylate;DTXSID60441793;AZVLZXHTXUIWRZ-VIFPVBQESA-N;(S)-1-tert-Butyl2-ethyl2,3-dihydro-1H-pyrrole-1,2-dicarboxylate;MFCD11501326;AKOS015909619;CS-O-10632;1H-Pyrrole-1,2-dicarboxylic acid, 2,3-dihydro-, 1-(1,1-dimethylethyl) 2-ethyl ester, (2S)-;AC-25292;AS-20004;CS-0021429;EN300-7098043;Ethyl (S)-1-Boc-2,3-dihydro-2-pyrrolecarboxylate;Ethyl (S)-1-Boc-2,3-dihydropyrrole-2-carboxylate;(5S)-1-(tert-Butoxycarbonyl)-2-pyrroline-5-carboxylic acid ethyl ester

Chemical Property of (S)-1-tert-Butyl 2-ethyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.49
• Boiling Point: 315.631 °C at 760 mmHg
• PKA: -2.52±0.40(Predicted)
• Flash Point: 144.689 °C
• PSA: 55.84000
• Density: 1.126 g/cm³
• LogP: 2.01050
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 241.13140809
• Heavy Atom Count: 17
• Complexity: 330

Purity/Quality:

98%, ^*data from raw suppliers

(S)-1-Boc-2,3-dihydro-2-pyrrolecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CC=CN1C(=O)OC(C)(C)C
• Isomeric SMILES: CCOC(=O)[C@@H]1CC=CN1C(=O)OC(C)(C)C

Technology Process of (S)-1-tert-Butyl 2-ethyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate

There total 6 articles about (S)-1-tert-Butyl 2-ethyl 2,3-dihydro-1H-pyrrole-1,2-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: 100.0%

(S)-ethyl N-tert-butoxycarbonylpyroglutamate (144978-35-8,144978-12-1,251924-83-1) → (5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester (178172-26-4)

Guidance literature:

(S)-ethyl N-tert-butoxycarbonylpyroglutamate; With lithium triethylborohydride; In tetrahydrofuran; toluene; at -45 ℃; for 0.5h; Large scale;

With dmap; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In tetrahydrofuran; toluene; at 25 ℃; for 3h; Large scale;

Reference yield: 70.0%

5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (194594-23-5) → (5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester (178172-26-4)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; at 160 - 180 ℃;

DOI:10.1021/jo960153y

Reference yield:

(2S)-1-t-butyl 2-ethyl 5-methoxypyrrolidine-1,2-dicarboxylate (194594-24-6) → (5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester (178172-26-4)

Guidance literature:

With ammonium chloride; at 150 ℃; under 20 - 100 Torr; Yield given;

DOI:10.1016/S0960-894X(98)00377-1

upstream raw materials:

L-Pyroglutamic acid

ethyl (S)-pyroglutamate

di-tert-butyl dicarbonate

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

Downstream raw materials:

3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.1^3,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester

saxagliptin

(R)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile

(2S,4S,5R)-2-[(2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Refernces

• 1、 Nirogi, Ramakrishna,Mohammed, Abdul Rasheed,Shinde, Anil K.,Ravella, Srinivasa Rao,Bogaraju, Narsimha,Subramanian, Ramkumar,Mekala, Venkat Reddy,Palacharla, Raghava Choudary,Muddana, Nageswararao,Thentu, Jagadeesh Babu,Bhyrapuneni, Gopinadh,Abraham, Renny,Jasti, Venkat. "Discovery and Development of 3-(6-Chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]hexane Hydrochloride (SUVN-911): A Novel, Potent, Selective, and Orally Active Neuronal Nicotinic Acetylcholine α4β2 Receptor Antagonist for the Treatment of Depression". . p. 2833 - 2853. Retrieved 2020/03/05.
• 2、 -. "PROCESS FOR PREPARING DIPEPTIDYL PEPTIDASE IV INHIBITORS AND INTERMEDIATES THEREFOR". Paragraph 0041; 0112. . Retrieved 2016/07/27.