(1R)-2-(4-methylphenyl)-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,6]decan-4-yl]ethan-1-amine hydrochloride

Base Information

• Chemical Name: (1R)-2-(4-methylphenyl)-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,6]decan-4-yl]ethan-1-amine hydrochloride
• CAS No.: 1173167-13-9
• Molecular Formula: C₁₉H₂₈BNO₂*ClH
• Molecular Weight: 349.709

Synonyms:(1R)-2-(4-methylphenyl)-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,6]decan-4-yl]ethan-1-amine hydrochloride

Chemical Property of (1R)-2-(4-methylphenyl)-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,6]decan-4-yl]ethan-1-amine hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-2-(4-methylphenyl)-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,6]decan-4-yl]ethan-1-amine hydrochloride

There total 5 articles about (1R)-2-(4-methylphenyl)-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,6]decan-4-yl]ethan-1-amine hydrochloride 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:

2-(4-methylbenzyl)boronic acid (+)-pinanediol ester → (1R)-2-(4-methylphenyl)-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]ethan-1-amine hydrochloride (1173167-13-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -110 - -95 °C / Inert atmosphere

1.2: Matteson Homologation / -100 - -95 °C / Inert atmosphere

1.3: Matteson Homologation / 1 h / -100 - 20 °C / Inert atmosphere

2.1: tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere

3.1: ethyl acetate; tert-butyl methyl ether / 2 h / -10 - 20 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; hexane; tert-butyl methyl ether; ethyl acetate; 1.1: |Matteson Homologation;

DOI:10.1021/acs.jmedchem.1c00604

Reference yield:

4,4,5,5-tetramethyl-2-[(4-methylphenyl)methyl]-1,3,2-dioxaborolane (356570-52-0) → (1R)-2-(4-methylphenyl)-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]ethan-1-amine hydrochloride (1173167-13-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tert-butyl methyl ether / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -110 - -95 °C / Inert atmosphere

2.2: Matteson Homologation / -100 - -95 °C / Inert atmosphere

2.3: Matteson Homologation / 1 h / -100 - 20 °C / Inert atmosphere

3.1: tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere

4.1: ethyl acetate; tert-butyl methyl ether / 2 h / -10 - 20 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; hexane; tert-butyl methyl ether; ethyl acetate; 2.1: |Matteson Homologation;

DOI:10.1021/acs.jmedchem.1c00604

Reference yield:

4-Methylbenzyl bromide (104-81-4) → (1R)-2-(4-methylphenyl)-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]ethan-1-amine hydrochloride (1173167-13-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane / 16 h / 85 °C / Inert atmosphere

2.1: tert-butyl methyl ether / 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -110 - -95 °C / Inert atmosphere

3.2: Matteson Homologation / -100 - -95 °C / Inert atmosphere

3.3: Matteson Homologation / 1 h / -100 - 20 °C / Inert atmosphere

4.1: tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere

5.1: ethyl acetate; tert-butyl methyl ether / 2 h / -10 - 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; hexane; tert-butyl methyl ether; ethyl acetate; 3.1: |Matteson Homologation;

DOI:10.1021/acs.jmedchem.1c00604

upstream raw materials:

hydrogenchloride

(1S)-1-chloro-2-(4-methylbenzyl)boronic acid (+)-pinanediol ester

4,4,5,5-tetramethyl-2-[(4-methylphenyl)methyl]-1,3,2-dioxaborolane

4-Methylbenzyl bromide

Downstream raw materials:

N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-2-phenyl]amino]carbonyl]-2-(4-methylphenyl)]-2-1,2,3,4-tetrahydro-naphthoiccarboxamide

N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-2-phenyl]amino]carbonyl]-2-(4-methylphenyl)]-1-(S)-(-)-1,2,3,4-tetrahydro-naphthoiccarboxamide

N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-2-(4-methylphenyl)ethyl]amino]carbonyl]-3-methylbutyl]-1-tert-butoxycarboxamide

N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-2-(4-methylphenyl)ethyl]amino]carbonyl]-2-phenyl]-1-acetylcarboxamide

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