(S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-pyrrolidine-2-carbaldehyde

Base Information

• Chemical Name: (S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-pyrrolidine-2-carbaldehyde
• CAS No.: 166451-19-0
• Molecular Formula: C₁₃H₁₄N₄O₄
• Molecular Weight: 290.279
• Mol file: 166451-19-0.mol

Synonyms:(S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-pyrrolidine-2-carbaldehyde

Chemical Property of (S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-pyrrolidine-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-pyrrolidine-2-carbaldehyde

There total 5 articles about (S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-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: 73.0%

(2-Azido-4-hydroxy-5-methoxy-phenyl)-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-methanone → (S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-pyrrolidine-2-carbaldehyde (166451-19-0)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1016/0040-4020(95)00222-T

Reference yield:

(S)-1-(4-Hydroxy-5-methoxy-2-nitro-benzoyl)-pyrrolidine-2-carbaldehyde (175409-51-5) → (S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-pyrrolidine-2-carbaldehyde (166451-19-0)

Guidance literature:

With sodium azide; In N,N,N,N,N,N-hexamethylphosphoric triamide; Ambient temperature;

DOI:10.1016/S0040-4039(96)01484-0

Reference yield:

methyl-(2S)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxylate (175409-49-1) → (S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-pyrrolidine-2-carbaldehyde (166451-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBAL-H / CH₂Cl₂ / 0.75 h / -78 °C

2: NaN₃ / hexamethylphosphoric acid triamide / 8 h / Ambient temperature

With sodium azide; diisobutylaluminium hydride; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1039/a701249g

upstream raw materials:

(S)-1-(4-Hydroxy-5-methoxy-2-nitro-benzoyl)-pyrrolidine-2-carbaldehyde

(S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-pyrrolidine-2-carboxylic acid methyl ester

methyl-(2S)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxylate

4-Hydroxy-5-methoxy-2-nitro-benzoyl chloride

Downstream raw materials:

(11aS)-8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one