(S)-3-(5-Methoxy-2-nitro-phenyl)-1,3-dimethyl-pyrrolidin-2-one

Base Information

• Chemical Name: (S)-3-(5-Methoxy-2-nitro-phenyl)-1,3-dimethyl-pyrrolidin-2-one
• CAS No.: 83618-67-1
• Molecular Formula: C₁₃H₁₆N₂O₄
• Molecular Weight: 264.281
• Mol file: 83618-67-1.mol

Synonyms:

Chemical Property of (S)-3-(5-Methoxy-2-nitro-phenyl)-1,3-dimethyl-pyrrolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(5-Methoxy-2-nitro-phenyl)-1,3-dimethyl-pyrrolidin-2-one

There total 7 articles about (S)-3-(5-Methoxy-2-nitro-phenyl)-1,3-dimethyl-pyrrolidin-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: 19.0%

(S)-3-(3-Methoxy-phenyl)-1,3-dimethyl-pyrrolidin-2-one (83287-32-5) → (S)-3-(5-Methoxy-2-nitro-phenyl)-1,3-dimethyl-pyrrolidin-2-one (83618-67-1) + (S)-3-(3-Methoxy-4-nitro-phenyl)-1,3-dimethyl-pyrrolidin-2-one (83287-31-4) + (S)-3-(3-Methoxy-2-nitro-phenyl)-1,3-dimethyl-pyrrolidin-2-one (83287-34-7)

Guidance literature:

With copper(II) nitrate; In acetic anhydride; at 5 - 10 ℃; for 0.5h; Title compound not separated from byproducts;

DOI:10.1248/cpb.30.2641

Reference yield:

3-methoxyphenylacetonitrile (19924-43-7) → (S)-3-(5-Methoxy-2-nitro-phenyl)-1,3-dimethyl-pyrrolidin-2-one (83618-67-1)

Guidance literature:

Multi-step reaction with 7 steps

1: lithium diisopropylamide / tetrahydrofuran / 1.) -78 deg C; 2.) to room temperature

2: potassium hydroxide / ethanol / 7 h / Heating

3: 80 percent / LDA / tetrahydrofuran / 1.) -78 deg C; 2.) to room temperature

4: hydrogen, trace of perchloric acid / 10percent palladized charcoal / methanol

5: 1.) methanolic potassium hydroxide; 2.) sodium periodate; 3.) sodium borohydride

6: 82 percent / H₂O / 12 h / 180 °C / in sealed tube

7: cupric nitrate trihydrate / acetic anhydride / 0.5 h / 5 - 10 °C

With potassium hydroxide; sodium tetrahydroborate; sodium periodate; perchloric acid; hydrogen; copper(II) nitrate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; acetic anhydride;

DOI:10.1248/cpb.30.2641

Reference yield:

(R)-5-Benzyloxy-4-hydroxy-2-(3-methoxy-phenyl)-pentanenitrile (83287-36-9,83287-37-0) → (S)-3-(5-Methoxy-2-nitro-phenyl)-1,3-dimethyl-pyrrolidin-2-one (83618-67-1)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium hydroxide / ethanol / 7 h / Heating

2: 80 percent / LDA / tetrahydrofuran / 1.) -78 deg C; 2.) to room temperature

3: hydrogen, trace of perchloric acid / 10percent palladized charcoal / methanol

4: 1.) methanolic potassium hydroxide; 2.) sodium periodate; 3.) sodium borohydride

5: 82 percent / H₂O / 12 h / 180 °C / in sealed tube

6: cupric nitrate trihydrate / acetic anhydride / 0.5 h / 5 - 10 °C

With potassium hydroxide; sodium tetrahydroborate; sodium periodate; perchloric acid; hydrogen; copper(II) nitrate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; acetic anhydride;

DOI:10.1248/cpb.30.2641

upstream raw materials:

(S)-3-(3-Methoxy-phenyl)-1,3-dimethyl-pyrrolidin-2-one

3-methoxyphenylacetonitrile

(-)-3-(3-methoxy-phenyl)-3-methyl-dihydro-furan-2-one

(3S,5R)-5-Hydroxymethyl-3-(3-methoxy-phenyl)-3-methyl-dihydro-furan-2-one