N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine

Base Information

• Chemical Name: N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine
• CAS No.: 864665-78-1
• Molecular Formula: C₂₀H₂₂N₂O₇
• Molecular Weight: 402.404
• Mol file: 864665-78-1.mol

Synonyms:N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine

Chemical Property of N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine

There total 3 articles about N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine 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: 90.0%

methyl-(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-hydroxypyrrolidine-2-carboxylate (382137-65-7) → N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine (864665-78-1)

Guidance literature:

methyl-(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-hydroxypyrrolidine-2-carboxylate; With lithium borohydride; In tetrahydrofuran; at 0 - 20 ℃; for 4.5h;

With hydrogenchloride; water; In tetrahydrofuran; at 0 ℃;

Reference yield:

4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid (60547-92-4) → N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine (864665-78-1)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 16 h / 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 16 h / -20 - 20 °C / Inert atmosphere

3: lithium borohydride / tetrahydrofuran / 4.5 h / 0 - 20 °C / Inert atmosphere

With lithium borohydride; oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.jmedchem.7b00736

Reference yield:

4-benzyloxy-5-methoxy-2-nitrobenzoyl chloride (64154-78-5) → N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine (864665-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 16 h / -20 - 20 °C / Inert atmosphere

2: lithium borohydride / tetrahydrofuran / 4.5 h / 0 - 20 °C / Inert atmosphere

With lithium borohydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.jmedchem.7b00736

upstream raw materials:

methyl-(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-hydroxypyrrolidine-2-carboxylate

4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid

4-benzyloxy-5-methoxy-2-nitrobenzoyl chloride

Downstream raw materials:

N-[2-amino-4-benzyloxy-5-methoxybenzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine

N-[4-benzyloxy-5-methoxy-2-(tert-butyloxycarbonylamino)benzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine