4-((1R,2R,3S,5S)-3-((hydroxy(phenyl)phosphoryl)oxy)-2-(methoxycarbonyl)-8-azabicyclo[3.2.1]octan-8-yl)-4-oxobutanoic acid trifluoroacetate salt

Base Information

• Chemical Name: 4-((1R,2R,3S,5S)-3-((hydroxy(phenyl)phosphoryl)oxy)-2-(methoxycarbonyl)-8-azabicyclo[3.2.1]octan-8-yl)-4-oxobutanoic acid trifluoroacetate salt
• CAS No.: 1431753-57-9
• Molecular Formula: C₂HF₃O₂*C₁₉H₂₄NO₈P
• Molecular Weight: 539.399
• Mol file: 1431753-57-9.mol

Synonyms:4-((1R,2R,3S,5S)-3-((hydroxy(phenyl)phosphoryl)oxy)-2-(methoxycarbonyl)-8-azabicyclo[3.2.1]octan-8-yl)-4-oxobutanoic acid trifluoroacetate salt

Chemical Property of 4-((1R,2R,3S,5S)-3-((hydroxy(phenyl)phosphoryl)oxy)-2-(methoxycarbonyl)-8-azabicyclo[3.2.1]octan-8-yl)-4-oxobutanoic acid trifluoroacetate salt

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((1R,2R,3S,5S)-3-((hydroxy(phenyl)phosphoryl)oxy)-2-(methoxycarbonyl)-8-azabicyclo[3.2.1]octan-8-yl)-4-oxobutanoic acid trifluoroacetate salt

There total 5 articles about 4-((1R,2R,3S,5S)-3-((hydroxy(phenyl)phosphoryl)oxy)-2-(methoxycarbonyl)-8-azabicyclo[3.2.1]octan-8-yl)-4-oxobutanoic acid trifluoroacetate salt 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: 85.0%

4-((1R,2R,3S,5S)-3-(((benzyloxy)(phenyl)phosphoryl)oxy)-2-(methoxycarbonyl)-8-azabicyclo[3.2.1]octan-8-yl)-4-oxobutanoic acid trifluoroacetate salt (1431753-56-8) → 4-((1R,2R,3S,5S)-3-((hydroxy(phenyl)phosphoryl)oxy)-2-(methoxycarbonyl)-8-azabicyclo[3.2.1]octan-8-yl)-4-oxobutanoic acid trifluoroacetate salt (1431753-57-9)

Guidance literature:

With hydrogen; palladium; In ethanol; at 20 ℃;

DOI:10.1021/jm400228w

Reference yield:

C13H12ClO2P (50972-25-3) → 4-((1R,2R,3S,5S)-3-((hydroxy(phenyl)phosphoryl)oxy)-2-(methoxycarbonyl)-8-azabicyclo[3.2.1]octan-8-yl)-4-oxobutanoic acid trifluoroacetate salt (1431753-57-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; cyclohexane / 16 h / 0 - 20 °C / Inert atmosphere

2.1: potassium carbonate / benzene / 80 °C / Inert atmosphere

3.1: zinc; formic acid / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

4.1: triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C / Inert atmosphere

4.2: 0.67 h

5.1: palladium; hydrogen / ethanol / 20 °C

With formic acid; hydrogen; potassium carbonate; palladium; triethylamine; zinc; lithium diisopropyl amide; In tetrahydrofuran; ethanol; cyclohexane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm400228w

Reference yield:

(1R,2R,3S,5S)-methyl 3-(((benzyloxy)(phenyl)phosphoryl)oxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate (148533-52-2) → 4-((1R,2R,3S,5S)-3-((hydroxy(phenyl)phosphoryl)oxy)-2-(methoxycarbonyl)-8-azabicyclo[3.2.1]octan-8-yl)-4-oxobutanoic acid trifluoroacetate salt (1431753-57-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / benzene / 80 °C / Inert atmosphere

2.1: zinc; formic acid / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3.1: triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C / Inert atmosphere

3.2: 0.67 h

4.1: palladium; hydrogen / ethanol / 20 °C

With formic acid; hydrogen; potassium carbonate; palladium; triethylamine; zinc; In ethanol; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm400228w

upstream raw materials:

C₁₃H₁₂ClO₂P

(1R,2R,3S,5S)-methyl 3-(((benzyloxy)(phenyl)phosphoryl)oxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

4-((1R,2R,3S,5S)-3-(((benzyloxy)(phenyl)phosphoryl)oxy)-2-(methoxycarbonyl)-8-azabicyclo[3.2.1]octan-8-yl)-4-oxobutanoic acid trifluoroacetate salt

methyl ecgonine

Refernces