(2S,4R)-1-(2-Azido-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde

Base Information

• Chemical Name: (2S,4R)-1-(2-Azido-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde
• CAS No.: 623583-15-3
• Molecular Formula: C₁₂H₁₁FN₄O₂
• Molecular Weight: 262.243
• Mol file: 623583-15-3.mol

Synonyms:(2S,4R)-1-(2-Azido-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde

Chemical Property of (2S,4R)-1-(2-Azido-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-1-(2-Azido-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde

There total 7 articles about (2S,4R)-1-(2-Azido-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde 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: 80.0%

(2-Azido-phenyl)-((2S,4R)-4-fluoro-2-hydroxymethyl-pyrrolidin-1-yl)-methanone (623583-12-0) → (2S,4R)-1-(2-Azido-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde (623583-15-3)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetlet.2003.08.075

Reference yield:

2-azidobenzoic acid (31162-13-7) → (2S,4R)-1-(2-Azido-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde (623583-15-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (COCl)2; DMF / CH₂Cl₂

1.2: 66 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

With oxalyl dichloride; Dess-Martin periodane; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1016/j.tetlet.2003.08.075

Reference yield:

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9) → (2S,4R)-1-(2-Azido-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde (623583-15-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 81 percent / DAST / CH₂Cl₂ / -78 - 20 °C

2.1: DIBAL-H / tetrahydrofuran / -78 - 20 °C

3.1: HCl; water / dioxane

4.1: (COCl)2; DMF / CH₂Cl₂

4.2: 66 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

With hydrogenchloride; oxalyl dichloride; water; diisobutylaluminium hydride; Dess-Martin periodane; N,N-dimethyl-formamide; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1016/j.tetlet.2003.08.075

upstream raw materials:

(2-Azido-phenyl)-((2S,4R)-4-fluoro-2-hydroxymethyl-pyrrolidin-1-yl)-methanone

2-azidobenzoic acid

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate