benzyl 2-(6-oxo-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-4-yl)-acetate

Base Information

• Chemical Name: benzyl 2-(6-oxo-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-4-yl)-acetate
• CAS No.: 1357495-82-9
• Molecular Formula: C₁₆H₁₅NO₃
• Molecular Weight: 269.3
• Mol file: 1357495-82-9.mol

Synonyms:benzyl 2-(6-oxo-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-4-yl)-acetate

Chemical Property of benzyl 2-(6-oxo-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-4-yl)-acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-(6-oxo-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-4-yl)-acetate

There total 6 articles about benzyl 2-(6-oxo-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-4-yl)-acetate 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: 57.0%

[(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2,36635-61-7) + benzyl 2-(4-oxocyclopent-2-en-1-yl)acetate (158604-58-1) → benzyl 2-(6-oxo-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-4-yl)-acetate (1357495-82-9)

Guidance literature:

[(p-methylphenyl)sulfonylmethyl]isonitrile; benzyl 2-(4-oxocyclopent-2-en-1-yl)acetate; With sodium hydride; In diethyl ether; dimethyl sulfoxide; at 20 ℃; for 2h; Inert atmosphere;

With water; In diethyl ether; dimethyl sulfoxide; at 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.12.013

Reference yield:

(1R*,2S*,3S*,5R*)-(±)-2-bromo-3-hydroxybicyclo[3.2.0]heptan-6-one (56011-39-3,71963-06-9,73346-97-1,73346-98-2,74524-00-8,89195-25-5) → benzyl 2-(6-oxo-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-4-yl)-acetate (1357495-82-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dihydrogen peroxide; acetic acid / dichloromethane / 20 °C / Inert atmosphere

2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 80 °C / Inert atmosphere

3.1: dimethyl sulfoxide; trifluoroacetic anhydride / dichloromethane / 0.83 h / -60 °C / Inert atmosphere

3.2: 1.5 h / -60 - 20 °C / Inert atmosphere

3.3: 20 °C / Inert atmosphere

4.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 4 h / 20 °C / Inert atmosphere

5.1: sodium hydride / diethyl ether; dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere

5.2: 0.33 h / 20 °C / Inert atmosphere

With dmap; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; In diethyl ether; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1016/j.tetlet.2011.12.013

Reference yield:

(3aR*,4S*,5S*,6aR*)-(±)-4-bromo-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one → benzyl 2-(6-oxo-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-4-yl)-acetate (1357495-82-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 80 °C / Inert atmosphere

2.1: dimethyl sulfoxide; trifluoroacetic anhydride / dichloromethane / 0.83 h / -60 °C / Inert atmosphere

2.2: 1.5 h / -60 - 20 °C / Inert atmosphere

2.3: 20 °C / Inert atmosphere

3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 4 h / 20 °C / Inert atmosphere

4.1: sodium hydride / diethyl ether; dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere

4.2: 0.33 h / 20 °C / Inert atmosphere

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; In diethyl ether; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1016/j.tetlet.2011.12.013

upstream raw materials:

[(p-methylphenyl)sulfonylmethyl]isonitrile

benzyl 2-(4-oxocyclopent-2-en-1-yl)acetate

2-(4-oxocyclopent-2-en-1-yl)acetic acid

bicyclo[3.2.0]hept-2-en-6-one