dibenzyl (2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: dibenzyl (2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate
• CAS No.: 1279110-13-2
• Molecular Formula: C₂₂H₂₂N₄O₄
• Molecular Weight: 406.441
• Mol file: 1279110-13-2.mol

Synonyms:dibenzyl (2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate

Chemical Property of dibenzyl (2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dibenzyl (2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate

There total 2 articles about dibenzyl (2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidine-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: 94.0%

dibenzyl (2S,4S)-4-(4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate (1279110-12-1) → dibenzyl (2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate (1279110-13-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1016/j.tet.2011.01.031

Reference yield:

(2S,4S)-Nα-Cbz-4-azidoproline benzyl ester (329191-55-1) → dibenzyl (2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate (1279110-13-2)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 20 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C

With tetrabutyl ammonium fluoride; copper(II) sulfate; sodium L-ascorbate; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.1016/j.tet.2011.01.031

Reference yield: 97.0%

dibenzyl (2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate (1279110-13-2) + methyl iodide (74-88-4) → 3-((3S,5S)-1,5-bis(benzyloxycarbonyl)pyrrolidin-3-yl)-1-methyl-3H-1,2,3-triazol-1-ium iodide (1279110-14-3)

Guidance literature:

In acetonitrile; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2011.01.031

upstream raw materials:

dibenzyl (2S,4S)-4-(4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate

(2S,4S)-N^α-Cbz-4-azidoproline benzyl ester

Downstream raw materials:

3-((3S,5S)-1,5-bis(benzyloxycarbonyl)pyrrolidin-3-yl)-1-methyl-3H-1,2,3-triazol-1-ium iodide