(R)-N-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide

Base Information

Chemical Name:(R)-N-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide
CAS No.:1443049-93-1
Molecular Formula:C₁₈H₂₈BNO₃
Molecular Weight:317.236
Hs Code.:

Synonyms:(R)-N-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide

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Chemical Property of (R)-N-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide

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Technology Process of (R)-N-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide

There total 12 articles about (R)-N-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide 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:

: 100-52-7
benzaldehyde

: 1443049-93-1
(R)-N-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: 1 h / 0 - 20 °C / Inert atmosphere

2.1: [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; C₄₅H₄₉O₄P / toluene / 0.33 h / 80 °C / Inert atmosphere

2.2: 14 h / 20 - 60 °C / Inert atmosphere

3.1: trimethylpyruvic acid / tetrahydrofuran; toluene / 1 h / 20 °C / Inert atmosphere

With C₄₅H₄₉O₄P; [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; trimethylpyruvic acid; In tetrahydrofuran; toluene;
DOI:10.1021/ja402569j

Reference yield:

: (R)-phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methanaminium chloride

: 3282-30-2
pivaloyl chloride

: 1443049-93-1
(R)-N-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide

Guidance literature:: (R)-phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methanaminium chloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; Schlenk technique;

pivaloyl chloride; In dichloromethane; at 0 - 20 ℃; Schlenk technique;
DOI:10.1021/acs.orglett.5b00934

Reference yield:

: 155396-71-7
tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate

: 1443049-93-1
(R)-N-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium carbonate; sodium sulfate / tetrahydrofuran / 18 h / Inert atmosphere; Reflux

2.1: sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; sodium t-butanolate; copper(l) chloride; (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diisopropylphosphine / tert-butyl methyl ether / 12 h / 20 °C / Schlenk technique

3.1: hydrogenchloride / dichloromethane; ethyl acetate / 0 °C / Schlenk technique

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Schlenk technique

4.2: 0 - 20 °C / Schlenk technique

With hydrogenchloride; (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diisopropylphosphine; potassium carbonate; sodium sulfate; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; N-ethyl-N,N-diisopropylamine; copper(l) chloride; sodium t-butanolate; In tetrahydrofuran; dichloromethane; tert-butyl methyl ether; ethyl acetate;
DOI:10.1021/acs.orglett.5b00934