(2S,4R)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde

Base Information

• Chemical Name: (2S,4R)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde
• CAS No.: 929049-03-6
• Molecular Formula: C₂₀H₁₉FN₂O₆
• Molecular Weight: 402.379
• Mol file: 929049-03-6.mol

Synonyms:(2S,4R)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde

Chemical Property of (2S,4R)-1-(4-Benzyloxy-5-methoxy-2-nitro-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-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde

There total 2 articles about (2S,4R)-1-(4-Benzyloxy-5-methoxy-2-nitro-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%

methyl-(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxylate (929049-02-5) → (2S,4R)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde (929049-03-6)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.75h;

DOI:10.1016/j.bmcl.2006.10.070

Reference yield:

methyl-(2S,4S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-hydroxypyrrolidine-2-carboxylate → (2S,4R)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde (929049-03-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / DAST / CH₂Cl₂ / 12 h / -78 - 20 °C

2: 80 percent / DIBAL-H / CH₂Cl₂ / 0.75 h / -78 °C

With diisobutylaluminium hydride; 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane;

DOI:10.1016/j.bmcl.2006.10.070

Reference yield: 85.0%

(2S,4R)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde (929049-03-6) + ethanethiol (75-08-1) → (2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal (929049-04-7)

Guidance literature:

With chloro-trimethyl-silane; In chloroform; at 20 ℃; for 24h;

DOI:10.1016/j.bmcl.2006.10.070

upstream raw materials:

methyl-(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxylate

Downstream raw materials:

(2S,4R)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal

(2-Amino-4-hydroxy-5-methoxy-phenyl)-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidin-1-yl]-methanone

(2S,4R)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]-4-fluoropyrrolidine-2-carboxaldehyde diethyl-dithioacetal

[2-Amino-4-(3-{5-amino-4-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-propoxy)-5-methoxy-phenyl]-[(2S,4R)-2-(bis-ethylsulfanyl-methyl)-4-fluoro-pyrrolidin-1-yl]-methanone