[(1S)-1-chloro-2-(3-ethylphenyl)ethyl]boronic acid (+)-pinane-2,3-diyl diester

Base Information

• Chemical Name: [(1S)-1-chloro-2-(3-ethylphenyl)ethyl]boronic acid (+)-pinane-2,3-diyl diester
• CAS No.: 1444010-71-2
• Molecular Formula: C₂₀H₂₈BClO₂
• Molecular Weight: 346.705
• Mol file: 1444010-71-2.mol

Synonyms:[(1S)-1-chloro-2-(3-ethylphenyl)ethyl]boronic acid (+)-pinane-2,3-diyl diester

Chemical Property of [(1S)-1-chloro-2-(3-ethylphenyl)ethyl]boronic acid (+)-pinane-2,3-diyl diester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S)-1-chloro-2-(3-ethylphenyl)ethyl]boronic acid (+)-pinane-2,3-diyl diester

There total 5 articles about [(1S)-1-chloro-2-(3-ethylphenyl)ethyl]boronic acid (+)-pinane-2,3-diyl diester 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: 99.0%

dichloromethane (75-09-2) + (3aS,4S,6S,7aR)-2-(3-ethylbenzyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (1444010-70-1) → [(1S)-1-chloro-2-(3-ethylphenyl)ethyl]boronic acid (+)-pinane-2,3-diyl diester (1444010-71-2)

Guidance literature:

dichloromethane; With n-butyllithium; In tetrahydrofuran; hexane; at -100 ℃; for 0.333333h;

(3aS,4S,6S,7aR)-2-(3-ethylbenzyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole; In tetrahydrofuran; hexane; at -100 ℃; for 0.333333h;

With zinc(II) chloride; In tetrahydrofuran; hexane; at -100 - 20 ℃; for 18.5h;

Reference yield:

1-(bromomethyl)-3-ethylbenzene (216658-62-7) → [(1S)-1-chloro-2-(3-ethylphenyl)ethyl]boronic acid (+)-pinane-2,3-diyl diester (1444010-71-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 12 h / 100 °C

2.1: diethyl ether / 12 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -100 °C

3.2: -100 - 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane;

Reference yield:

2-(3-ethylbenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1444010-69-8) → [(1S)-1-chloro-2-(3-ethylphenyl)ethyl]boronic acid (+)-pinane-2,3-diyl diester (1444010-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diethyl ether / 12 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -100 °C

2.2: -100 - 20 °C

With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane;

upstream raw materials:

dichloromethane

(3aS,4S,6S,7aR)-2-(3-ethylbenzyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole

(3-Bromophenyl)methanol

1-(bromomethyl)-3-ethylbenzene

Downstream raw materials:

N-((R)-2-(3-ethylphenyl)-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethyl)-1,1,1-trimethyl-N-(trimethylsilyl)silanamine

[(1R)-1-amino-2-(3-ethylphenyl)ethyl]boronic acid (+)-pinane-2,3-diyl diester trifluoroacetate

[(1R)-1-[(4-biphenyl-4-yl-4-oxobutanoyl)amino]-2-(3-ethylphenyl)ethyl]boronic acid

[(1R)-1-[(4-biphenyl-4-yl-4-oxobutanoyl)amino]-2-(3-ethylphenyl)ethyl]boronic acid (+)-pinane-2,3-diyl diester