fluoren-9-ylmethyl 4-hydroxy-5-(hydroxymethyl)-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate

Base Information

• Chemical Name: fluoren-9-ylmethyl 4-hydroxy-5-(hydroxymethyl)-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate
• CAS No.: 954127-67-4
• Molecular Formula: C₃₃H₃₁N₃O₇
• Molecular Weight: 581.625
• Mol file: 954127-67-4.mol

Synonyms:fluoren-9-ylmethyl 4-hydroxy-5-(hydroxymethyl)-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate

Chemical Property of fluoren-9-ylmethyl 4-hydroxy-5-(hydroxymethyl)-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of fluoren-9-ylmethyl 4-hydroxy-5-(hydroxymethyl)-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate

There total 13 articles about fluoren-9-ylmethyl 4-hydroxy-5-(hydroxymethyl)-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate 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: 67.0%

fluoren-9-ylmethyl 4-(tert-butyldimethylsilanyloxy)-5-(tert-butyldimethylsilanyloxymethyl)-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate (954127-66-3) → fluoren-9-ylmethyl 4-hydroxy-5-(hydroxymethyl)-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate (954127-67-4)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 24h;

DOI:10.1002/ejoc.200700217

Reference yield:

5-bromopyridin-2-ol (13466-38-1) → fluoren-9-ylmethyl 4-hydroxy-5-(hydroxymethyl)-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate (954127-67-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 93 percent / Ag₂CO₃ / tetrahydrofuran / 5 h / Heating

2.1: nBuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 809 mg / tetrahydrofuran; hexane / 2 h / -78 °C

3.1: 352 mg / H₂ / Pd/C / methanol / 0.5 h / 20 °C

4.1: 80 percent / aq. NaHCO₃ / tetrahydrofuran; dioxane / 1.5 h / 20 °C

5.1: 35 percent / Ph₃P; DIAD / dioxane / 8 h / 20 °C

6.1: 67 percent / aq. HCl / methanol / 24 h / 20 °C

With hydrogenchloride; n-butyllithium; di-isopropyl azodicarboxylate; hydrogen; sodium hydrogencarbonate; triphenylphosphine; silver carbonate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane;

DOI:10.1002/ejoc.200700217

Reference yield:

(4S,5R)-4-{[(tert-butyl)dimethylsilyl]oxy}-5-{[(tert-butyl)dimethylsilyl]oxymethyl}-1-azacyclopent-1-ene (954127-62-9) → fluoren-9-ylmethyl 4-hydroxy-5-(hydroxymethyl)-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate (954127-67-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: nBuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 809 mg / tetrahydrofuran; hexane / 2 h / -78 °C

2.1: 352 mg / H₂ / Pd/C / methanol / 0.5 h / 20 °C

3.1: 80 percent / aq. NaHCO₃ / tetrahydrofuran; dioxane / 1.5 h / 20 °C

4.1: 35 percent / Ph₃P; DIAD / dioxane / 8 h / 20 °C

5.1: 67 percent / aq. HCl / methanol / 24 h / 20 °C

With hydrogenchloride; n-butyllithium; di-isopropyl azodicarboxylate; hydrogen; sodium hydrogencarbonate; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane;

DOI:10.1002/ejoc.200700217

upstream raw materials:

fluoren-9-ylmethyl 4-(tert-butyldimethylsilanyloxy)-5-(tert-butyldimethylsilanyloxymethyl)-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate

5-bromopyridin-2-ol

4-(tert-butyldimethylsilanyloxy)-5-(tert-butyldimethylsilanyloxymethyl)-2-(2-oxopyridin-5-yl)pyrrolidine

fluoren-9-ylmethyl 4-(tert-butyldimethylsilanyloxy)-5-(tert-butyldimethylsilanyloxymethyl)-2-(2-oxopyridin-5-yl)pyrrolidine-1-carboxylate

Downstream raw materials:

fluoren-9-ylmethyl 5-[bis(4-methoxyphenyl)(phenyl)methoxymethyl]-4-hydroxy-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate

Refernces