(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

Base Information

• Chemical Name: (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
• CAS No.: 1395322-91-4
• Molecular Formula: C₁₉H₂₂FN₅O₄
• Molecular Weight: 403.413
• Mol file: 1395322-91-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 12 articles about (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 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:

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] (1417820-60-0) → (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 (1395322-91-4)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 4h;

DOI:10.1111/j.1747-0285.2012.01404.x

Reference yield:

2-(2-fluoro-4-nitrophenyl)-5-oxohexahydrocyclopenta[c]pyrrole (1395322-86-7) → (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 (1395322-91-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: toluene-4-sulfonic acid / water; benzene / 3 h / Reflux; Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C

3.1: sodium hydrogencarbonate / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C

4.2: 12 h / -78 - 20 °C

5.1: triethylamine / dichloromethane / 4 h / 0 - 20 °C

6.1: sodium azide / N,N-dimethyl-formamide / 4 h / 80 °C

With n-butyllithium; sodium azide; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1111/j.1747-0285.2012.01404.x

Reference yield:

2-(2-fluoro-4-nitrophenyl)-hexahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane] (1395322-87-8) → (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 (1395322-91-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C

2.1: sodium hydrogencarbonate / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C

3.2: 12 h / -78 - 20 °C

4.1: triethylamine / dichloromethane / 4 h / 0 - 20 °C

5.1: sodium azide / N,N-dimethyl-formamide / 4 h / 80 °C

With n-butyllithium; sodium azide; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1111/j.1747-0285.2012.01404.x

upstream raw materials:

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

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

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

Downstream raw materials:

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

N-(((5S)-3-(3-fluoro-4-(5-oxohexahydrocyclopenta[c]pyrrol-2(1H)-yl)phenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide

(5R)-5-((1H-1,2,3-triazol-1-yl)methyl)-3-(3-fluoro-4-(5-oxohexahydrocyclopenta[c]pyrrol-2(1H)-yl)phenyl)oxazolidin-2-one

N-(((5S)-3-(3-fluoro-4-(5-(hydroxyimino)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)phenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide