N-[[(5S)-3-[4-(5-cyanomethyl-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Base Information

• Chemical Name: N-[[(5S)-3-[4-(5-cyanomethyl-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
• CAS No.: 1395323-02-0
• Molecular Formula: C₂₁H₂₃FN₄O₃
• Molecular Weight: 398.437

Synonyms:N-[[(5S)-3-[4-(5-cyanomethyl-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Chemical Property of N-[[(5S)-3-[4-(5-cyanomethyl-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of N-[[(5S)-3-[4-(5-cyanomethyl-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

There total 14 articles about N-[[(5S)-3-[4-(5-cyanomethyl-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 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: 30.0%

N-(((5S)-3-(3-fluoro-4-(5-oxohexahydrocyclopenta[c]pyrrol-2(1H)-yl)phenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide (1395322-94-7) + cyanoacetic acid (372-09-8) → N-[[(5S)-3-[4-(5-cyanomethyl-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (1395323-02-0)

Guidance literature:

With ammonium acetate; In benzene; for 20h; Reflux;

DOI:10.1111/j.1747-0285.2012.01404.x

Reference yield:

2-(2-fluoro-4-nitrophenyl)-5-oxohexahydrocyclopenta[c]pyrrole (1395322-86-7) → N-[[(5S)-3-[4-(5-cyanomethyl-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (1395323-02-0)

Guidance literature:

Multi-step reaction with 9 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

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

8.1: toluene-4-sulfonic acid / water; acetone / 6 h / Reflux

9.1: ammonium acetate / benzene / 20 h / Reflux

With pyridine; n-butyllithium; sodium azide; palladium 10% on activated carbon; ammonium acetate; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; 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) → N-[[(5S)-3-[4-(5-cyanomethyl-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (1395323-02-0)

Guidance literature:

Multi-step reaction with 8 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

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

7.1: toluene-4-sulfonic acid / water; acetone / 6 h / Reflux

8.1: ammonium acetate / benzene / 20 h / Reflux

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

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

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