(3'S,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester

Base Information

• Chemical Name: (3'S,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester
• CAS No.: 1265907-55-8
• Molecular Formula: C₂₇H₃₄Cl₂N₂O₆
• Molecular Weight: 553.483
• Mol file: 1265907-55-8.mol

Synonyms:(3'S,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester

Chemical Property of (3'S,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3'S,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester

There total 10 articles about (3'S,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl 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: 84.0%

6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5',6'-dihydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester (1265907-54-7) → (3'S,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester (1265907-55-8)

Guidance literature:

With tetrafluoroboric acid diethyl ether; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); Josiphos SL-J₂₁₂-1; hydrogen; In tetrahydrofuran; dichloromethane; at 15 ℃; for 20h; under 41372.9 Torr; optical yield given as %ee; enantioselective reaction; Autoclave; Large scale reaction;

DOI:10.1021/jo102070e

Reference yield:

5-bromo-2-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]pyridine (945999-98-4) → (3'S,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester (1265907-55-8)

Guidance literature:

Multi-step reaction with 3 steps

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / N,N-dimethyl acetamide / 20 h / 80 - 85 °C / Inert atmosphere; Large scale reaction

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane; water / 1.08 h / 50 - 83 °C / Inert atmosphere; Large scale reaction

3: tetrafluoroboric acid diethyl ether; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); Josiphos SL-J₂₁₂-1; hydrogen / tetrahydrofuran; dichloromethane / 20 h / 15 °C / 41372.9 Torr / Autoclave; Large scale reaction

With tetrafluoroboric acid diethyl ether; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; Josiphos SL-J₂₁₂-1; hydrogen; potassium acetate; sodium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl acetamide; water; 2: Suzuki coupling;

DOI:10.1021/jo102070e

Reference yield:

2-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (1206625-60-6) → (3'S,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester (1265907-55-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane; water / 1.08 h / 50 - 83 °C / Inert atmosphere; Large scale reaction

2: tetrafluoroboric acid diethyl ether; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); Josiphos SL-J₂₁₂-1; hydrogen / tetrahydrofuran; dichloromethane / 20 h / 15 °C / 41372.9 Torr / Autoclave; Large scale reaction

With tetrafluoroboric acid diethyl ether; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); tetrakis(triphenylphosphine) palladium⁽⁰⁾; Josiphos SL-J₂₁₂-1; hydrogen; sodium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; 1: Suzuki coupling;

DOI:10.1021/jo102070e

upstream raw materials:

5-bromo-2-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]pyridine

6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5',6'-dihydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester

6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-1'-(2,2,2-trifluoroacetyl)-1',2',5',6'-tetrahydro-[3,4']bipyridinyl-3'-carboxylic acid ethyl ester

C₂₄H₂₅Cl₂F₃N₂O₅

Downstream raw materials:

MK-1597

(3'R,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-1',2',3',4',5',6'-hexahydro-[3,4']bipyridinyl-3'-carboxylic acid [2-chloro-5-(2-methoxy-ethyl)benzyl]cyclopropylamide acetate

C₂₇H₃₄Cl₂N₂O₆

(3'R,4'S)-3'-{[2-chloro-5-(2-methoxy-ethyl)-benzyl]cyclopropylcarbamoyl}-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester