cis-Dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate

Base Information

• Chemical Name: cis-Dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate
• CAS No.: 87813-06-7
• Molecular Formula: C15H19 N O4
• Molecular Weight: 277.32
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50450596
• Nikkaji Number: J184.265J
• Wikidata: Q63409159
• Mol file: 87813-06-7.mol

Synonyms:87813-06-7;cis-Dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate;Dimethyl (3R,4S)-1-benzylpyrrolidine-3,4-dicarboxylate;cis-Dimethyl 1-benzyl-3,4-pyrrolidinedicarboxylate;dimethyl (cis)-1-benzylpyrrolidine-3,4-dicarboxylate;(3R,4S)-Dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate;cis-Dimethyl1-benzyl-3,4-pyrrolidinedicarboxylate;SCHEMBL585357;DTXSID50450596;JSRVVUSBZJFOJO-BETUJISGSA-N;3,4-dimethyl (3R,4S)-1-benzylpyrrolidine-3,4-dicarboxylate;MFCD09910273;AKOS015919806;CS-10815;CS-0135537;F15699;A862408;dimethyl cis-1-benzyl-3,4-pyrrolidinedicarboxylate;dimethyl cis-1-benzylpyrrolidine-3,4-dicarboxylate;Q63409159;F1967-3057;N-BENZYL-CIS-3,4-DI(METHOXYCARBONYL)PYRR0LIDINE;Dimethyl(cis)-1-(phenylmethyl)-3,4-pyrrolidinedicarboxylate;Dimethyl (cis)-1-(phenylmethyl)-3,4-pyrrolidinedicarboxylate;rel-Dimethyl (3R,4S)-1-benzylpyrrolidine-3,4-dicarboxylate;(3alpha,4alpha)-1-Benzylpyrrolidine-3,4-dicarboxylic acid dimethyl ester;(3R,4S)-rel-1-(phenylmethyl)-3,4-pyrrolidinedicarboxylicacid 3,4-dimethyl ester;3,4-Pyrrolidinedicarboxylicacid, 1-(phenylmethyl)-, 3,4-dimethyl ester, (3R,4S)-rel-

Chemical Property of cis-Dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.539
• Boiling Point: 366.056°C at 760 mmHg
• Flash Point: 175.184°C
• PSA: 55.84000
• Density: 1.189g/cm³
• LogP: 1.01850
• Storage Temp.: 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 277.13140809
• Heavy Atom Count: 20
• Complexity: 328

Purity/Quality:

98%min ^*data from raw suppliers

Dimethyl(cis)-1-benzylpyrrolidine-3,4-dicarboxylate >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CN(CC1C(=O)OC)CC2=CC=CC=C2
• Isomeric SMILES: COC(=O)[C@@H]1CN(C[C@@H]1C(=O)OC)CC2=CC=CC=C2

Technology Process of cis-Dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate

There total 21 articles about cis-Dimethyl 1-benzylpyrrolidine-3,4-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: 100.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + N-benzylglycine (17136-36-6) + dimethylfumarate (624-49-7) → dimethyl (3R,4R)-1-benzylpyrrolidine-3,4-dicarboxylate (87813-05-6,87813-06-7,111186-67-5)

Guidance literature:

In toluene; for 0.25h; Heating;

DOI:10.1246/bcsj.60.4079

Reference yield: 97.0%

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) + dimethylfumarate (624-49-7) → dimethyl (3R,4R)-1-benzylpyrrolidine-3,4-dicarboxylate (87813-05-6,87813-06-7,111186-67-5)

Guidance literature:

trifluoroacetic acid; In dichloromethane; for 3h; Product distribution; Ambient temperature; further catalyst, reaction time;

Reference yield: 96.0%

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) + 1,4-dimethyl but-2-enedioate (23055-10-9) → dimethyl (3R,4R)-1-benzylpyrrolidine-3,4-dicarboxylate (87813-05-6,87813-06-7,111186-67-5)

Guidance literature:

With lithium fluoride; In acetonitrile;

DOI:10.1016/j.bmcl.2009.09.044

upstream raw materials:

formaldehyd

N-benzylglycine

dimethyl cis-but-2-ene-1,4-dioate

N-benzyl-N-(cyanomethyl)-N-[(trimethylsilyl)methyl]amine

Downstream raw materials:

dimethyl (3R,4R)-1-benzylpyrrolidine-3,4-dicarboxylate

(3R,4R)-1-Benzyl-pyrrolidine-3,4-dicarboxylic acid monomethyl ester

dimethyl pyrrolidine-3,4-dicarboxylate

racemic trans-1-(tert-butoxycarbonyl)pyrrolidine-3,4-dicarboxylic acid

Refernces

• 1、 Morin,Wang, Ying,Jones, Brian T.,Mifune, Yuto,Su, Lijing,Shi, Hexin,Moresco, Eva Marie Y.,Zhang, Hong,Beutler, Bruce,Boger, Dale L.. "Diprovocims: A New and Exceptionally Potent Class of Toll-like Receptor Agonists". supporting information. p. 14440 - 14454. Retrieved 2018/10/24.
• 2、 Thaqi, Ali,Scott, Janet L.,Gilbert, Jayne,Sakoff, Jennette A.,McCluskey, Adam. "Synthesis and biological activity of Δ-5,6-norcantharimides: importance of the 5,6-bridge". supporting information; experimental part. p. 1717 - 1723. Retrieved 2010/07/02.