(2S,4R)-1-tert-butyl 2-methyl 4-cyanopyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (2S,4R)-1-tert-butyl 2-methyl 4-cyanopyrrolidine-1,2-dicarboxylate
• CAS No.: 194163-91-2
• Molecular Formula: C12H18 N2 O4
• Molecular Weight: 254.286
• Hs Code.: 2933998090
• European Community (EC) Number: 689-913-9
• DSSTox Substance ID: DTXSID20592159
• Wikidata: Q72459191
• Mol file: 194163-91-2.mol

Synonyms:194163-91-2;N-BOC-TRANS-4-CYANO-L-PROLINE METHYL ESTER;(2S,4R)-1-tert-butyl 2-methyl 4-cyanopyrrolidine-1,2-dicarboxylate;Boc-trans-4-cyano-L-proline methyl ester;1-(tert-butyl) 2-methyl (2s,4r)-4-cyanopyrrolidine-1,2-dicarboxylate;1-O-tert-butyl 2-O-methyl (2S,4R)-4-cyanopyrrolidine-1,2-dicarboxylate;MFCD03094915;GHLKJIQVORAVHE-IUCAKERBSA-N;SCHEMBL7727212;DTXSID20592159;1-tert-butyl 2-methyl (2S,4R)-4-cyanopyrrolidine-1,2-dicarboxylate;AKOS015850923;AKOS015907656;AS-41210;CS-0449260;A26547;n-tert-butoxycarbonyl-trans-4-cyano-l-proline methyl ester;(4R)-1-(tert-Butyloxycarbonyl)-4-cyano-L-Proline Methyl Ester;1,2-Pyrrolidinedicarboxylicacid,4-cyano-,1-(1,1-dimethylethyl)2-methyl ester,(2S,4R)-

Chemical Property of (2S,4R)-1-tert-butyl 2-methyl 4-cyanopyrrolidine-1,2-dicarboxylate

Chemical Property:

• PSA: 79.63000
• Density: 1.17
• LogP: 1.24648
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 254.12665706
• Heavy Atom Count: 18
• Complexity: 391

Purity/Quality:

97% ^*data from raw suppliers

N-Boc-trans-4-cyano-L-prolinemethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)OC)C#N
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)C#N

Technology Process of (2S,4R)-1-tert-butyl 2-methyl 4-cyanopyrrolidine-1,2-dicarboxylate

There total 2 articles about (2S,4R)-1-tert-butyl 2-methyl 4-cyanopyrrolidine-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:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → 1-(tert-butyl) 2-methyl (2S,4R)-4-cyanopyrrolidine-1 ,2-dicarboxylate (194163-91-2)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 16.5 h / 0 - 25 °C

2: triethylamine / dichloromethane / 16 h / 0 - 25 °C

3: dimethyl sulfoxide / 16 h / 80 °C

With triethylamine; In dichloromethane; dimethyl sulfoxide;

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → 1-(tert-butyl) 2-methyl (2S,4R)-4-cyanopyrrolidine-1 ,2-dicarboxylate (194163-91-2) + (2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (487048-28-2)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / acetonitrile / 0 - 20 °C

2: triethylamine / dichloromethane / 20 h / 0 - 20 °C

3: dimethyl sulfoxide / 4 h / 80 °C

With triethylamine; In dichloromethane; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/anie.201302014

Reference yield: 95.0%

1-(tert-butyl) 2-methyl (2S,4R)-4-cyanopyrrolidine-1 ,2-dicarboxylate (194163-91-2) + benzyl ((4-(aminomethyl)phenyl)(imino)methyl)carbamate hydrochloride → tert-butyl (2S,4R)-2-((4-(N-((benzyloxy)carbonyl)carbamimidoyl)benzyl)carbamoyl)-4-cyanopyrrolidine-1-carboxylate

Guidance literature:

1-(tert-butyl) 2-methyl (2S,4R)-4-cyanopyrrolidine-1 ,2-dicarboxylate; With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In dichloromethane; for 1h;

benzyl ((4-(aminomethyl)phenyl)(imino)methyl)carbamate hydrochloride; With sodium hydrogencarbonate; In dichloromethane; water; for 1h;

upstream raw materials:

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

(4R)-1-(tert-Butyloxycarbonyl)-4-(aminomethyl)-L-Proline Methyl Ester

1-(tert-butyl) 2,4-dimethyl (2S,4R)-pyrrolidine-1,2,4-tricarboxylate

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