N-(2-cyanoethyl)-2-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]bicyclo[2.2.2]oct-1-yl}acetamide

Base Information

Chemical Name:N-(2-cyanoethyl)-2-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]bicyclo[2.2.2]oct-1-yl}acetamide
CAS No.:1414867-50-7
Molecular Formula:C₂₅H₃₅BN₂O₃
Molecular Weight:422.375
Hs Code.:

Synonyms:N-(2-cyanoethyl)-2-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]bicyclo[2.2.2]oct-1-yl}acetamide

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Chemical Property of N-(2-cyanoethyl)-2-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]bicyclo[2.2.2]oct-1-yl}acetamide

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Technology Process of N-(2-cyanoethyl)-2-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]bicyclo[2.2.2]oct-1-yl}acetamide

There total 4 articles about N-(2-cyanoethyl)-2-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]bicyclo[2.2.2]oct-1-yl}acetamide 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: 85.0%

: 151-18-8,60585-38-8
2-cyanoethylamine

: 1414867-49-4
2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)bicyclo[2.2.2] octan-1-yl)acetic acid

: 1414867-50-7
N-(2-cyanoethyl)-2-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]bicyclo[2.2.2]oct-1-yl}acetamide

Guidance literature:: With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; at 20 ℃; for 48h;
DOI:10.1021/jm301296t

Reference yield:

: 70631-58-2
methyl 2-(4-phenylbicyclo[2.2.2]octan-1-yl)acetate

: 1414867-50-7
N-(2-cyanoethyl)-2-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]bicyclo[2.2.2]oct-1-yl}acetamide

Guidance literature:: Multi-step reaction with 4 steps

1: [bis-(trifluoroacetoxy)iodo]benzene; iodine / chloroform / 1.5 h / 20 °C

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere

3: sodium hydroxide / methanol; water / 0.5 h / 120 °C

4: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane / 48 h / 20 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; [bis-(trifluoroacetoxy)iodo]benzene; iodine; potassium acetate; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; sodium hydroxide; In methanol; dichloromethane; chloroform; water; dimethyl sulfoxide;
DOI:10.1021/jm301296t

Reference yield:

: 1166828-27-8
methyl 2-(4-(4-iodophenyl)bicyclo[2.2.2]octan-1-yl)acetate

: 1414867-50-7
N-(2-cyanoethyl)-2-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]bicyclo[2.2.2]oct-1-yl}acetamide

Guidance literature:: Multi-step reaction with 3 steps

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere

2: sodium hydroxide / methanol; water / 0.5 h / 120 °C

3: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane / 48 h / 20 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; sodium hydroxide; In methanol; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1021/jm301296t