2-(2-fluoro-4-nitrophenyl)-5-oxohexahydrocyclopenta[c]pyrrole

Base Information

• Chemical Name: 2-(2-fluoro-4-nitrophenyl)-5-oxohexahydrocyclopenta[c]pyrrole
• CAS No.: 1395322-86-7
• Molecular Formula: C₁₃H₁₃FN₂O₃
• Molecular Weight: 264.256
• Mol file: 1395322-86-7.mol

Synonyms:2-(2-fluoro-4-nitrophenyl)-5-oxohexahydrocyclopenta[c]pyrrole

Chemical Property of 2-(2-fluoro-4-nitrophenyl)-5-oxohexahydrocyclopenta[c]pyrrole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2-fluoro-4-nitrophenyl)-5-oxohexahydrocyclopenta[c]pyrrole

There total 3 articles about 2-(2-fluoro-4-nitrophenyl)-5-oxohexahydrocyclopenta[c]pyrrole 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: 95.0%

2-(2-fluoro-4-nitrophenyl)-octahydro-5-hydroxycyclopenta[c]pyrrole (1395322-85-6) → 2-(2-fluoro-4-nitrophenyl)-5-oxohexahydrocyclopenta[c]pyrrole (1395322-86-7)

Guidance literature:

2-(2-fluoro-4-nitrophenyl)-octahydro-5-hydroxycyclopenta[c]pyrrole; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1.5h;

With triethylamine; In dichloromethane; at -78 - 20 ℃; for 2h;

Reference yield:

t-butyl 5-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-cyclopenteno[c]pyrrole-2-carboxylate (203663-25-6) → 2-(2-fluoro-4-nitrophenyl)-5-oxohexahydrocyclopenta[c]pyrrole (1395322-86-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / methanol / 1 h / 20 °C

2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 6 h / Reflux

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C

With hydrogenchloride; oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; acetonitrile;

DOI:10.1111/j.1747-0285.2012.01404.x

Reference yield:

octahydro-5-hydroxycyclopenta[c]pyrrole hydrochloride (1417820-59-7,1323417-56-6) → 2-(2-fluoro-4-nitrophenyl)-5-oxohexahydrocyclopenta[c]pyrrole (1395322-86-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 6 h / Reflux

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C

With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;

DOI:10.1111/j.1747-0285.2012.01404.x

upstream raw materials:

t-butyl 5-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-cyclopenteno[c]pyrrole-2-carboxylate

octahydro-5-hydroxycyclopenta[c]pyrrole hydrochloride

2-(2-fluoro-4-nitrophenyl)-octahydro-5-hydroxycyclopenta[c]pyrrole

Downstream raw materials:

2-(4-amino-2-fluorophenyl)-hexahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane]

(5R)-3-(3-fluoro-4-(tetrahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane]-2(3H)-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one

2-[2-fluoro-4-[(5R)-5-[[(methylsulfonyl)oxy]methyl]-2-oxo-3-oxazolidinyl]phenyl]-hexahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane]

(5R)-5-(azidomethyl)-3-(3-fluoro-4-(tetrahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane]-2(3H)-yl)phenyl)-oxazolidin-2-one