(2R)-N-(cyanomethyl)-4-methyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pentanamide

Base Information

Chemical Name:(2R)-N-(cyanomethyl)-4-methyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pentanamide
CAS No.:597584-57-1
Molecular Formula:C₂₀H₂₉BN₂O₃
Molecular Weight:356.273
Hs Code.:

Synonyms:(2R)-N-(cyanomethyl)-4-methyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pentanamide

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Chemical Property of (2R)-N-(cyanomethyl)-4-methyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pentanamide

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Technology Process of (2R)-N-(cyanomethyl)-4-methyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pentanamide

There total 2 articles about (2R)-N-(cyanomethyl)-4-methyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pentanamide 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:

: 73183-34-3
bis(pinacol)diborane

: 513246-85-0
(2R)-2-(3-bromophenyl)-N-(cyanomethyl)-4-methylpentanamide

: (2S)-N-(cyanomethyl)-4-methyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pentanamide

: 597584-57-1
(2R)-N-(cyanomethyl)-4-methyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pentanamide

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 85 - 90 ℃; for 3h; Title compound not separated from byproducts;
DOI:10.1021/jm0301078

Reference yield:

: 513246-79-2
(2R)-2-(3-bromophenyl)-4-methylpentanoic acid

: 597584-57-1
(2R)-N-(cyanomethyl)-4-methyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pentanamide

Guidance literature:: Multi-step reaction with 2 steps

1: PyBOP; Et₃N / dimethylformamide / 18 h / 20 °C

2: KOAc; PdCl₂(dppf) / dimethylformamide / 3 h / 85 - 90 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; potassium acetate; triethylamine; In N,N-dimethyl-formamide;
DOI:10.1021/jm0301078

Reference yield: 41.0%

: 4-(4-bromophenyl)quinuclidine

: 597584-57-1
(2R)-N-(cyanomethyl)-4-methyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pentanamide

: (2R)-2-[4'-(1-azabicyclo[2.2.2]oct-4-yl)-1,1'-biphenyl-3-yl]-N-(cyanomethyl)-4-methylpentanamide

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In N,N-dimethyl-formamide; at 80 - 95 ℃;
DOI:10.1021/jm0301078