(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(methylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Base Information

• Chemical Name: (1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(methylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
• CAS No.: 857086-94-3
• Molecular Formula: C₃₂H₃₁BrN₂O₂
• Molecular Weight: 555.514
• Mol file: 857086-94-3.mol

Synonyms:(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Chemical Property of (1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(methylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Chemical Property:

• Solubility.: DCM, Toluene

Purity/Quality:

(αR,βR)-6-Bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-3-quinolineethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (αR,βR)-6-Bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-3-quinolineethanol is an intermediate in the synthesis of (αS,βR)-Bedaquiline (B119540), a diarylquinoline derivative that acts as a mycobacterial inhibitor.

Technology Process of (1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(methylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

There total 13 articles about (1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(methylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol 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:

(2R)-2-(6-bromo-2-methoxyquinolin-3-yl)-1-(naphthalen-1-yl)-2-phenylethanone (1298044-25-3) → bedaquiline (843663-66-1,654653-93-7,857086-92-1) + (1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol (857086-94-3,654653-93-7,857086-92-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C

1.2: 0.5 h

2.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C

3.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C

4.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C

5.1: tetrahydrofuran / 24 h / 45 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; copper(I) bromide dimethylsulfide complex; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 1.2: Barbier type reaction;

DOI:10.1002/ejoc.201001720

Reference yield:

(1R)-1-(6-bromo-2-methoxyquinolin-3-yl)-2-(naphthalen-1-yl)-1-phenylpent-4-en-2-ol (1298044-27-5) → bedaquiline (843663-66-1,654653-93-7,857086-92-1) + (1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol (857086-94-3,654653-93-7,857086-92-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C

2: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C

3: triethylamine / dichloromethane / 3 h / 0 - 20 °C

4: tetrahydrofuran / 24 h / 45 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1002/ejoc.201001720

Reference yield:

C30H24BrNO3 (1298044-29-7) → bedaquiline (843663-66-1,654653-93-7,857086-92-1) + (1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol (857086-94-3,654653-93-7,857086-92-1)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C

2: triethylamine / dichloromethane / 3 h / 0 - 20 °C

3: tetrahydrofuran / 24 h / 45 °C

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/ejoc.201001720

upstream raw materials:

(2R)-2-(6-bromo-2-methoxyquinolin-3-yl)-1-(naphthalen-1-yl)-2-phenylethanone

(1R)-1-(6-bromo-2-methoxyquinolin-3-yl)-2-(naphthalen-1-yl)-1-phenylpent-4-en-2-ol

C₃₀H₂₄BrNO₃

(4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-(naphthalen-1-yl)-4-phenylbutane-1,3-diol

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