(S)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-methylpyrrolidin-2-one

Base Information

• Chemical Name: (S)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-methylpyrrolidin-2-one
• CAS No.: 1295626-74-2
• Molecular Formula: C₁₇H₂₃NO₃
• Molecular Weight: 289.375
• Mol file: 1295626-74-2.mol

Synonyms:(S)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-methylpyrrolidin-2-one

Chemical Property of (S)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-methylpyrrolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-methylpyrrolidin-2-one

There total 9 articles about (S)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-methylpyrrolidin-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: 63.0%

(S)-rolipram (85416-73-5) + methyl iodide (74-88-4) → (S)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-methylpyrrolidin-2-one (1295626-74-2)

Guidance literature:

(S)-rolipram; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.166667h; Inert atmosphere;

methyl iodide; In N,N-dimethyl-formamide; mineral oil; for 16h; Inert atmosphere;

DOI:10.1021/jm200070e

Reference yield:

C18H18O4 (121174-59-2) → (S)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-methylpyrrolidin-2-one (1295626-74-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Triphenylphosphine oxide; N,N,N',N'-tetramethylguanidine / 24 h / 75 °C / Inert atmosphere

2.1: sodium hydroxide / methanol; water / 16 h / 0 - 20 °C / Inert atmosphere

3.1: thionyl chloride / dichloromethane / 16 h / Inert atmosphere; Reflux

4.1: dichloromethane / 2 h / Reflux; Inert atmosphere

5.1: palladium 10% on activated carbon; hydrogen / ethanol; ethyl acetate / 90 °C / 67506.8 Torr

6.1: para-xylene / 36 h / 160 °C / Inert atmosphere; Autoclave

7.1: potassium carbonate / N,N-dimethyl-formamide / 40 h / 60 °C / Inert atmosphere

8.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 20 °C / Inert atmosphere

8.2: 16 h / Inert atmosphere

With thionyl chloride; palladium 10% on activated carbon; hydrogen; sodium hydride; potassium carbonate; Triphenylphosphine oxide; sodium hydroxide; N,N,N',N'-tetramethylguanidine; In methanol; ethanol; dichloromethane; para-xylene; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jm200070e

Reference yield:

3-(3-benzyloxy-4-methoxyphenyl)-4-nitrobutanoic acid (1295626-42-4) → (S)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-methylpyrrolidin-2-one (1295626-74-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: thionyl chloride / dichloromethane / 16 h / Inert atmosphere; Reflux

2.1: dichloromethane / 2 h / Reflux; Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / ethanol; ethyl acetate / 90 °C / 67506.8 Torr

4.1: para-xylene / 36 h / 160 °C / Inert atmosphere; Autoclave

5.1: potassium carbonate / N,N-dimethyl-formamide / 40 h / 60 °C / Inert atmosphere

6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 20 °C / Inert atmosphere

6.2: 16 h / Inert atmosphere

With thionyl chloride; palladium 10% on activated carbon; hydrogen; sodium hydride; potassium carbonate; In ethanol; dichloromethane; para-xylene; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jm200070e

upstream raw materials:

C₁₈H₁₈O₄

3-(3-benzyloxy-4-methoxyphenyl)-4-nitrobutanoic acid

3-(3-(benzyloxy)-4-methoxyphenyl)-4-nitrobutanoyl chloride

(S)-3-(3-benzyloxy-4-methoxyphenyl)-4-nitro-N-[(S)-1-phenylethyl]butanamide

Refernces