3-(4-((4-((4,4-dimethylpiperidin-1-yl)methyl)benzyl)oxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Base Information

• Chemical Name: 3-(4-((4-((4,4-dimethylpiperidin-1-yl)methyl)benzyl)oxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione
• CAS No.: 1323405-51-1
• Molecular Formula: C₂₈H₃₃N₃O₄
• Molecular Weight: 475.588

Synonyms:3-(4-((4-((4,4-dimethylpiperidin-1-yl)methyl)benzyl)oxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Chemical Property of 3-(4-((4-((4,4-dimethylpiperidin-1-yl)methyl)benzyl)oxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Chemical Property:

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Technology Process of 3-(4-((4-((4,4-dimethylpiperidin-1-yl)methyl)benzyl)oxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione

There total 13 articles about 3-(4-((4-((4,4-dimethylpiperidin-1-yl)methyl)benzyl)oxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione 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: 27.0%

methyl 5-amino-4-(4-(4-((4,4-dimethylpiperidin-1-yl)methyl)benzyloxy)-1-oxoisoindolin-2-yl)-5-oxopentanoate (1323410-26-9) → 3-(4-((4-((4,4-dimethylpiperidin-1-yl)methyl)benzyl)oxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione (1323405-51-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; Cooling with ice;

Reference yield:

methyl 4,5-diamino-5-oxo-pentanoate hydrochloride (1323290-64-7) → 3-(4-((4-((4,4-dimethylpiperidin-1-yl)methyl)benzyl)oxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione (1323405-51-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere

2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere

2.2: 0.17 h / 20 °C / Inert atmosphere

3.1: di-isopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 1 h / 0 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Inert atmosphere

5.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / Inert atmosphere; Cooling with ice

With di-isopropyl azodicarboxylate; potassium tert-butylate; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.jmedchem.9b01928

Reference yield:

3-hydroxy 2-methylbenzoic acid (603-80-5) → 3-(4-((4-((4,4-dimethylpiperidin-1-yl)methyl)benzyl)oxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione (1323405-51-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sulfuric acid / 17 h / 65 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 1 h / 25 °C / Inert atmosphere

3.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / ethyl acetate / 2 h / 65 °C / Inert atmosphere; Irradiation

4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere

5.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere

5.2: 0.17 h / 20 °C / Inert atmosphere

6.1: di-isopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

6.2: 1 h / 0 °C / Inert atmosphere

7.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Inert atmosphere

8.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / Inert atmosphere; Cooling with ice

With 1H-imidazole; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; sulfuric acid; potassium tert-butylate; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.jmedchem.9b01928

upstream raw materials:

methyl 5-amino-4-(4-(4-((4,4-dimethylpiperidin-1-yl)methyl)benzyloxy)-1-oxoisoindolin-2-yl)-5-oxopentanoate

methyl 4,5-diamino-5-oxo-pentanoate hydrochloride

3-hydroxy 2-methylbenzoic acid

methyl 3-hydroxy-2-methylbenzoate

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