4-(N-BOC-N-METHYL-AMINOMETHYL)-PHENYLBORONIC ACID PINACOL ESTER

Base Information

• Chemical Name: 4-(N-BOC-N-METHYL-AMINOMETHYL)-PHENYLBORONIC ACID PINACOL ESTER
• CAS No.: 936728-17-5
• Molecular Formula: C19H32BNO5
• Molecular Weight: 347.262
• Mol file: 936728-17-5.mol

Synonyms:4-(N-BOC-N-METHYL-AMINOMETHYL)-PHENYLBORONIC ACID PINACOL ESTER;tert-butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate

Chemical Property of 4-(N-BOC-N-METHYL-AMINOMETHYL)-PHENYLBORONIC ACID PINACOL ESTER

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

4-(N-Boc-N-methylaminomethyl)phenylboronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-(N-Boc-N-methylaminomethyl)phenylboronic acid pinacol ester

Technology Process of 4-(N-BOC-N-METHYL-AMINOMETHYL)-PHENYLBORONIC ACID PINACOL ESTER

There total 5 articles about 4-(N-BOC-N-METHYL-AMINOMETHYL)-PHENYLBORONIC ACID PINACOL 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: 94.0%

tert-butyl (4-bromobenzyl)(methyl)carbamate (260809-26-5) + bis(pinacol)diborane (73183-34-3) → tert-butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate (936728-17-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 14h; Inert atmosphere;

DOI:10.1021/acs.orglett.1c02770

Reference yield:

4-bromo-benzaldehyde (1122-91-4) → tert-butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate (936728-17-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: methanol; ethanol / 3 h / 20 °C

1.2: 3 h / 0 °C

2.1: dmap / tetrahydrofuran / 15.5 h / 0 - 20 °C

3.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 14 h / 80 °C / Inert atmosphere

With dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol;

DOI:10.1021/acs.orglett.1c02770

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate (936728-17-5)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap / tetrahydrofuran / 15.5 h / 0 - 20 °C

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 14 h / 80 °C / Inert atmosphere

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

DOI:10.1021/acs.orglett.1c02770

upstream raw materials:

tert-butyl (4-bromobenzyl)(methyl)carbamate

bis(pinacol)diborane

4-bromo-benzaldehyde

di-tert-butyl dicarbonate

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