(2S,4S)-4-cyano-2-{5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,4S)-4-cyano-2-{5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 1256390-80-3
• Molecular Formula: C₂₅H₃₃BN₄O₄
• Molecular Weight: 464.372

Synonyms:(2S,4S)-4-cyano-2-{5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (2S,4S)-4-cyano-2-{5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2S,4S)-4-cyano-2-{5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 3 articles about (2S,4S)-4-cyano-2-{5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester 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:

(2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (132622-71-0) → (2S,4S)-4-cyano-2-{5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (1256390-80-3)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / acetonitrile / 3 h / 20 °C

2: ammonium acetate / xylene / 140 °C / Inert atmosphere; Sealed tube

3: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / 110 °C / Inert atmosphere; Sealed tube

With ammonium acetate; potassium acetate; N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; acetonitrile; xylene;

Reference yield:

(2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (487048-28-2) → (2S,4S)-4-cyano-2-{5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (1256390-80-3)

Guidance literature:

Multi-step reaction with 4 steps

1: water; lithium hydroxide / 3 h / 40 °C

2: N-ethyl-N,N-diisopropylamine / acetonitrile / 3 h / 20 °C

3: ammonium acetate / xylene / 140 °C / Inert atmosphere; Sealed tube

4: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / 110 °C / Inert atmosphere; Sealed tube

With ammonium acetate; water; potassium acetate; N-ethyl-N,N-diisopropylamine; lithium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; acetonitrile; xylene;

Reference yield:

(2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 2-[2-(4-bromo-phenyl)-2-oxo-ethyl]ester 1-tert-butyl ester (1399845-09-0) → (2S,4S)-4-cyano-2-{5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (1256390-80-3)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium acetate / xylene / 140 °C / Inert atmosphere; Sealed tube

2: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / 110 °C / Inert atmosphere; Sealed tube

With ammonium acetate; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; xylene;

upstream raw materials:

(2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

(2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 2-[2-(4-bromo-phenyl)-2-oxo-ethyl]ester 1-tert-butyl ester

Downstream raw materials:

[(2S,5S)-2-(5-{4'-[2-((2S,4S)-4-cyano-pyrrolidin-2-yl)-3H-imidazol-4-yl]-biphenyl-4-yl}-1H-imidazol-2-yl)-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl]-carbamic acid methyl ester hydrochloride

{(2S,5S)-2-[5-(4'-{2-[(2S,4S)-4-cyano-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester

(2S,4S)-4-Cyano-2-(5-{4'-[2-((2S,5S)-5-methoxycarbonylamino-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-2-yl)-3H-imidazol-4-yl]-biphenyl-4-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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