tert-butyl (2S)-2-[5-(4-buta-1,3-diyn-1-ylphenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (2S)-2-[5-(4-buta-1,3-diyn-1-ylphenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate
• CAS No.: 1380290-32-3
• Molecular Formula: C₂₂H₂₃N₃O₂
• Molecular Weight: 361.444
• Mol file: 1380290-32-3.mol

Synonyms:tert-butyl (2S)-2-[5-(4-buta-1,3-diyn-1-ylphenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate

Chemical Property of tert-butyl (2S)-2-[5-(4-buta-1,3-diyn-1-ylphenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S)-2-[5-(4-buta-1,3-diyn-1-ylphenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate

There total 2 articles about tert-butyl (2S)-2-[5-(4-buta-1,3-diyn-1-ylphenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate 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:

tert-butyl (2S)-2-(5-{4-[4-(trimethylsilyl)buta-1,3-diyn-1-yl]phenyl}-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (1380290-30-1) → tert-butyl (2S)-2-[5-(4-buta-1,3-diyn-1-ylphenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate (1380290-32-3)

Guidance literature:

With methanol; potassium carbonate; In tetrahydrofuran; for 2h;

Reference yield:

tert-butyl (S)-2-[5-(4-iodophenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate (1242094-29-6) → tert-butyl (2S)-2-[5-(4-buta-1,3-diyn-1-ylphenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate (1380290-32-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methyllithium lithium bromide / diethyl ether / 20 °C / Inert atmosphere

1.2: 12 h / 40 °C / Inert atmosphere

2.1: potassium carbonate; methanol / tetrahydrofuran / 2 h

With methanol; methyllithium lithium bromide; potassium carbonate; In tetrahydrofuran; diethyl ether;

Reference yield: 57.0%

(S)-2-(4-iodo-1H-imidazol-2-yl)pyrrolidine-1-carboxylic acid tert-butyl ester (1228552-62-2) + tert-butyl (2S)-2-[5-(4-buta-1,3-diyn-1-ylphenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate (1380290-32-3) → tert-butyl (2S)-2-{5-[4-(4-{2-[(2S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]-1H-imidazol-5-yl}buta-1,3-diyn-1-yl)phenyl]-1H-imidazol-2-yl}pyrrolidine-1-carboxylate (1380290-33-4)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In tetrahydrofuran; at 40 ℃; for 15h;

DOI:10.1021/jm500951r

upstream raw materials:

tert-butyl (S)-2-[5-(4-iodophenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate

tert-butyl (2S)-2-(5-{4-[4-(trimethylsilyl)buta-1,3-diyn-1-yl]phenyl}-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

Downstream raw materials:

[(1S)-1-[[(2S)-2-[5-[4-[4-[2-[(2S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-2-pyrrolidinyl]-1H-imidazol-5-yl]-1,3-butadiynyl]phenyl]-1H-imidazol-2-yl]-1-pyrrolidinyl]carbonyl]-2-methylpropyl]carbamic acid methyl ester

2-[(2S)-pyrrolidin-2-yl]-5-[4-(4-{2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-5-yl}buta-1,3-diyn-1-yl)phenyl]-1H-imidazole

tert-butyl (2S)-2-{5-[4-(4-{2-[(2S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]-1H-imidazol-5-yl}buta-1,3-diyn-1-yl)phenyl]-1H-imidazol-2-yl}pyrrolidine-1-carboxylate