(S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-mesitylethane-1,2-diamine

Base Information

• Chemical Name: (S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-mesitylethane-1,2-diamine
• CAS No.: 1358742-39-8
• Molecular Formula: C₂₈H₄₅N₃OSi
• Molecular Weight: 467.77

Synonyms:(S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-mesitylethane-1,2-diamine

Chemical Property of (S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-mesitylethane-1,2-diamine

Chemical Property:

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Technology Process of (S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-mesitylethane-1,2-diamine

There total 10 articles about (S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-mesitylethane-1,2-diamine 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: 74.0%

(S)-(1-(2-(2-(mesitylamino)ethylamino)phenyl)pyrrolidin-2-yl)methanol (1358742-37-6) + tert-butyldimethylsilyl chloride (18162-48-6) → (S)-N1-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N2-mesitylethane-1,2-diamine (1358742-39-8)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.11.015

Reference yield:

2-(2,4,6-trimethylphenylamino)-2-oxoacetic acid (79354-46-4) → (S)-N1-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N2-mesitylethane-1,2-diamine (1358742-39-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / tetrahydrofuran; dichloromethane / 1 h / 0 °C / Inert atmosphere; Molecular sieve

1.2: 0 - 20 °C / Inert atmosphere; Molecular sieve

2.1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere; Cooling with ice; Reflux

2.2: Inert atmosphere

3.1: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With 1H-imidazole; lithium aluminium tetrahydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2011.11.015

Reference yield:

(S)-2-((tert-butyldimethylsilyloxy)methyl)-1-(2-nitrophenyl)pyrrolidine (1358742-08-1) → (S)-N1-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N2-mesitylethane-1,2-diamine (1358742-39-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 4 h / 3800.26 Torr

2.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / tetrahydrofuran; dichloromethane / 1 h / 0 °C / Inert atmosphere; Molecular sieve

2.2: 0 - 20 °C / Inert atmosphere; Molecular sieve

3.1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere; Cooling with ice; Reflux

3.2: Inert atmosphere

4.1: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With 1H-imidazole; lithium aluminium tetrahydride; palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1016/j.tetasy.2011.11.015

upstream raw materials:

2-(2,4,6-trimethylphenylamino)-2-oxoacetic acid

(S)-2-((tert-butyldimethylsilyloxy)methyl)-1-(2-nitrophenyl)pyrrolidine

(S)-2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)aniline

(S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-mesityloxalamide

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