(S)-1,2,8,8a-tetrahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizin-3(5H)-one

Base Information

• Chemical Name: (S)-1,2,8,8a-tetrahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizin-3(5H)-one
• CAS No.: 1301743-53-2
• Molecular Formula: C₂₃H₂₅NO₄
• Molecular Weight: 379.456
• Mol file: 1301743-53-2.mol

Synonyms:(S)-1,2,8,8a-tetrahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizin-3(5H)-one

Chemical Property of (S)-1,2,8,8a-tetrahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizin-3(5H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1,2,8,8a-tetrahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizin-3(5H)-one

There total 15 articles about (S)-1,2,8,8a-tetrahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizin-3(5H)-one 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: 77.0%

(S)-1,2,3,5,8,8a-hexahydro-6-(4-methoxyphenyl)-3-oxoindolizin-7-yl-trifluoromethanesulfonate (1301743-57-6) + 3,4-Dimethoxyphenylboronic acid (122775-35-3) → (S)-1,2,8,8a-tetrahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizin-3(5H)-one (1301743-53-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; water; at 85 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201100125

Reference yield:

benzyl (S)-2-(3-methoxy-3-oxopropyl)-5-(4-methoxyphenyl)-3-oxo-4-(tributylstannyl)-3,6-dihydropyridine-1(2H)-carboxylate → (S)-1,2,8,8a-tetrahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizin-3(5H)-one (1301743-53-2)

Guidance literature:

Multi-step reaction with 5 steps

1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere; Schlenk technique

2: sodium tetrahydroborate; cerium(III) chloride heptahydrate; methanol / 0 °C

3: palladium 10% on activated carbon; hydrogen / water; methanol / 20 °C

4: 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine / toluene / 12 h / 80 °C / Inert atmosphere

5: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 12 h / -78 - 20 °C / Inert atmosphere

With methanol; triethylsilane; sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; hydrogen; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: |Stille Cross Coupling / 2: |Luche Cerium Reduction;

DOI:10.1021/acs.orglett.9b04479

Reference yield:

tributyl[2-(4-methoxyphenyl)ethynyl]stannane → (S)-1,2,8,8a-tetrahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizin-3(5H)-one (1301743-53-2)

Guidance literature:

Multi-step reaction with 6 steps

1: triphenylphosphine; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾ / 1,4-dioxane / Inert atmosphere; Schlenk technique; Heating

2: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere; Schlenk technique

3: sodium tetrahydroborate; cerium(III) chloride heptahydrate; methanol / 0 °C

4: palladium 10% on activated carbon; hydrogen / water; methanol / 20 °C

5: 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine / toluene / 12 h / 80 °C / Inert atmosphere

6: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 12 h / -78 - 20 °C / Inert atmosphere

With methanol; triethylsilane; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; hydrogen; triphenylphosphine; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2: |Stille Cross Coupling / 3: |Luche Cerium Reduction;

DOI:10.1021/acs.orglett.9b04479

upstream raw materials:

(6R,8aS)-hexahydro-6-(4-methoxyphenyl)indolizine-3,7-dione

(S)-1,2,3,5,8,8a-hexahydro-6-(4-methoxyphenyl)-3-oxoindolizin-7-yl-trifluoromethanesulfonate

3,4-Dimethoxyphenylboronic acid

methyl 3-(2-((2S, 3R)-2-hydroxy-3-(4-methoxyphenyl)-4-nitrobutyl)-1,3-dioxolan-2-yl)propanoate

Downstream raw materials:

(S)-1,2,3,5,8,8a-hexahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizine