TERT-BUTYL 3-CYANOACETYL-1-PYRROLIDINECARBOXYLATE

Base Information

• Chemical Name: TERT-BUTYL 3-CYANOACETYL-1-PYRROLIDINECARBOXYLATE
• CAS No.: 660406-89-3
• Molecular Formula: C₁₂H₁₈N₂O₃
• Molecular Weight: 238.287
• Hs Code.: 2933990090
• Mol file: 660406-89-3.mol

Synonyms:AB3356;TERT-BUTYL 3-CYANOACETYL-1-PYRROLIDINECARBOXYLATE;

Chemical Property of TERT-BUTYL 3-CYANOACETYL-1-PYRROLIDINECARBOXYLATE

Chemical Property:

• PSA: 70.40000
• LogP: 1.66408

Purity/Quality:

98% ^*data from raw suppliers

1-Boc-3-(cyanoacetyl)pyrrolidine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of TERT-BUTYL 3-CYANOACETYL-1-PYRROLIDINECARBOXYLATE

There total 5 articles about TERT-BUTYL 3-CYANOACETYL-1-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:

methyl 1-tert-butoxycarbonyl-3-pyrrolidinecarboxylate (122684-33-7) + acetonitrile (75-05-8,26809-02-9) → tert-butyl 3-(2-cyanoacetyl)pyrrolidine-1-carboxylate (660406-89-3)

Guidance literature:

With sodium t-butanolate; In tetrahydrofuran; at 23 ℃; for 1.5h;

DOI:10.1021/acs.jmedchem.5b01072

Reference yield:

C13H19N3O3 + acetonitrile (75-05-8,26809-02-9) → tert-butyl 3-(2-cyanoacetyl)pyrrolidine-1-carboxylate (660406-89-3)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.bmcl.2010.10.114

Reference yield:

1-benzylpyrrolidine-3-carboxylic acid methyl ester (17012-21-4) → tert-butyl 3-(2-cyanoacetyl)pyrrolidine-1-carboxylate (660406-89-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ammonium formate / 5%-palladium/activated carbon / methanol; water / 2 h / Heating / reflux

2.1: dmap / dichloromethane / 13 h / 0 °C

3.1: n-butyllithium / tetrahydrofuran / -78 °C

3.2: 10 h / -78 °C

With dmap; n-butyllithium; ammonium formate; 5%-palladium/activated carbon; In tetrahydrofuran; methanol; dichloromethane; water;

upstream raw materials:

methyl 1-tert-butoxycarbonyl-3-pyrrolidinecarboxylate

acetonitrile

methyl pyrrolidine-3-carboxylate

1-benzylpyrrolidine-3-carboxylic acid methyl ester

Refernces

• 1、 Dwyer, Michael P.,Paruch, Kamil,Labroli, Marc,Alvarez, Carmen,Keertikar, Kerry M.,Poker, Cory,Rossman, Randall,Fischmann, Thierry O.,Duca, Jose S.,Madison, Vincent,Parry, David,Davis, Nicole,Seghezzi, Wolfgang,Wiswell, Derek,Guzi, Timothy J.. "Discovery of pyrazolo[1,5-a]pyrimidine-based CHK1 inhibitors: A template-based approach - Part 1". scheme or table. p. 471 - 474. Retrieved 2011/02/26.