(S)-5-acetoxymethyl-3-formyl-1-(2-nitro-benzoyl)-2-pyrroline

Base Information

• Chemical Name: (S)-5-acetoxymethyl-3-formyl-1-(2-nitro-benzoyl)-2-pyrroline
• CAS No.: 135159-24-9
• Molecular Formula: C₁₅H₁₄N₂O₆
• Molecular Weight: 318.286
• Mol file: 135159-24-9.mol

Synonyms:(S)-5-acetoxymethyl-3-formyl-1-(2-nitro-benzoyl)-2-pyrroline

Chemical Property of (S)-5-acetoxymethyl-3-formyl-1-(2-nitro-benzoyl)-2-pyrroline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-acetoxymethyl-3-formyl-1-(2-nitro-benzoyl)-2-pyrroline

There total 8 articles about (S)-5-acetoxymethyl-3-formyl-1-(2-nitro-benzoyl)-2-pyrroline 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: 100.0%

(S)-5-acetoxymethyl-1-(2-nitro-benzoyl)-2-pyrroline (135159-21-6) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → (S)-5-acetoxymethyl-3-formyl-1-(2-nitro-benzoyl)-2-pyrroline (135159-24-9)

Guidance literature:

With trichlorophosphate; In dichloromethane; at 0 ℃; for 3.5h;

DOI:10.1016/S0040-4020(01)00197-1

Reference yield:

Acetic acid (2S,5S)-5-methoxy-1-(2-nitro-benzoyl)-pyrrolidin-2-ylmethyl ester (135159-20-5) → (S)-5-acetoxymethyl-3-formyl-1-(2-nitro-benzoyl)-2-pyrroline (135159-24-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / quinoleinium camphosulfonate (QCS) / toluene / Heating

2: POCl₃ / 2.5 h / Ambient temperature

With trichlorophosphate; quinoleinium camphosulfonate; In toluene;

DOI:10.1016/S0040-4039(00)79689-4

Reference yield:

(5S)-5-[(1-ethoxyethyl)oxymethyl]tetrahydro-1H-2-pyrrolone (67040-46-4) → (S)-5-acetoxymethyl-3-formyl-1-(2-nitro-benzoyl)-2-pyrroline (135159-24-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaH; KI / tetrahydrofuran / 1.5 h / 20 °C

1.2: 95 percent / tetrahydrofuran / 0.17 h / 20 °C

2.1: 80 percent / DIBAL-H / toluene / 0.17 h / -78 °C

3.1: p-toluenesulfonic acid / CH₂Cl₂; methanol / 0.25 h / 0 °C

4.1: pyridine / 1 h / 20 °C

5.1: 94 percent / quinoleinium camphosulfonate / toluene / 2 h / 110 °C

6.1: 100 percent / POCl₃ / CH₂Cl₂ / 3.5 h / 0 °C

With pyridine; quinoleinium camphosulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; potassium iodide; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; toluene; 6.1: Vilsmeier-Haack reaction;

DOI:10.1016/S0040-4020(01)00197-1

upstream raw materials:

(S)-5-acetoxymethyl-1-(2-nitro-benzoyl)-2-pyrroline

N,N-dimethyl-formamide

(5S)-5-(1-ethoxy-ethoxymethyl)-1-(2-nitro-benzoyl)-pyrrolidin-2-ol

(5S)-5-(1-ethoxy-ethoxymethyl)-1-(2-nitro-benzoyl)-pyrrolidin-2-one

Downstream raw materials:

(S)-3-[2-(dimethylphosphono)-ethenyl]-5-formyl-1-(2-nitro-benzoyl)-2-pyrroline

(S)-3-[2-(dimethylphosphono)-ethenyl]-5-hydroxymethyl-1-(2-nitro-benzoyl)-2-pyrroline

(E)-3-[(S)-5-Hydroxymethyl-1-(2-nitro-benzoyl)-4,5-dihydro-1H-pyrrol-3-yl]-N,N-dimethyl-acrylamide

N-(2-nitrobenzoyl)pyrrolidine carboxaldehyde