benzyl 1-(3-{(2R)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl}propyl)-1H-imidazole-5-carboxylate

Base Information

• Chemical Name: benzyl 1-(3-{(2R)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl}propyl)-1H-imidazole-5-carboxylate
• CAS No.: 1422064-14-9
• Molecular Formula: C₂₈H₃₃N₃O₅
• Molecular Weight: 491.587

Synonyms:benzyl 1-(3-{(2R)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl}propyl)-1H-imidazole-5-carboxylate

Chemical Property of benzyl 1-(3-{(2R)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl}propyl)-1H-imidazole-5-carboxylate

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Technology Process of benzyl 1-(3-{(2R)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl}propyl)-1H-imidazole-5-carboxylate

There total 9 articles about benzyl 1-(3-{(2R)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl}propyl)-1H-imidazole-5-carboxylate 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: 55.0%

1H-imidazole-4(5)-carboxylic acid phenylmethyl ester (1208114-68-4) + 3-{(2R)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl}propyl 4-methylbenzenesulfonate (1422064-12-7) → benzyl 1-(3-{(2R)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl}propyl)-1H-imidazole-5-carboxylate (1422064-14-9) + benzyl 1-(3-{(2R)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl}propyl)-1H-imidazole-4-carboxylate (1422064-15-0)

Guidance literature:

1H-imidazole-4⁽⁵⁾-carboxylic acid phenylmethyl ester; With caesium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 0.5h; Inert atmosphere;

3-{(2R)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl}propyl 4-methylbenzenesulfonate; In N,N-dimethyl-formamide; at 50 ℃; Inert atmosphere;

DOI:10.3390/molecules18010050

Reference yield:

[4-(2-methoxyethoxy)phenyl]methanol (79407-30-0) → benzyl 1-(3-{(2R)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl}propyl)-1H-imidazole-5-carboxylate (1422064-14-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: phosphorus tribromide / diethyl ether / 20 °C / Inert atmosphere; Cooling with ice

2.1: sodium hydride / tetrahydrofuran; paraffin oil / 24.25 h / 0 - 20 °C / Inert atmosphere

3.1: lithium borohydride / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 0 - 20 °C

5.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 50 °C / Inert atmosphere

5.2: 50 °C / Inert atmosphere

With lithium borohydride; phosphorus tribromide; sodium hydride; caesium carbonate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; paraffin oil;

DOI:10.3390/molecules18010050

Reference yield:

methyl 3-{(2S)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl} propanoate (1422064-10-5) → benzyl 1-(3-{(2R)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl}propyl)-1H-imidazole-5-carboxylate (1422064-14-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium borohydride / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 0 - 20 °C

3.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 50 °C / Inert atmosphere

3.2: 50 °C / Inert atmosphere

With lithium borohydride; caesium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.3390/molecules18010050

upstream raw materials:

[4-(2-methoxyethoxy)phenyl]methanol

methyl 3-{(2S)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl} propanoate

1-(bromomethyl)-4-(2-methoxyethoxy)benzene

methyl 3-[(2S)-5-oxopyrrolidin-2-yl]propanoate

Downstream raw materials:

1-(3-{(2R)-1-[4-(2-methoxyethoxy)benzyl]-5-oxopyrrolidin-2-yl}propyl)-1H-imidazole-5-carboxylic acid

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