(S)-2,3,9,9a-tetrahydro-8-(3,4-dimethoxyphenyl)-7-(4-methoxyphenyl)-1H-quinolizin-4(6H)-one

Base Information

Chemical Name:(S)-2,3,9,9a-tetrahydro-8-(3,4-dimethoxyphenyl)-7-(4-methoxyphenyl)-1H-quinolizin-4(6H)-one
CAS No.:1394132-10-5
Molecular Formula:C₂₄H₂₇NO₄
Molecular Weight:393.483
Hs Code.:

Synonyms:(S)-2,3,9,9a-tetrahydro-8-(3,4-dimethoxyphenyl)-7-(4-methoxyphenyl)-1H-quinolizin-4(6H)-one

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Chemical Property of (S)-2,3,9,9a-tetrahydro-8-(3,4-dimethoxyphenyl)-7-(4-methoxyphenyl)-1H-quinolizin-4(6H)-one

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Technology Process of (S)-2,3,9,9a-tetrahydro-8-(3,4-dimethoxyphenyl)-7-(4-methoxyphenyl)-1H-quinolizin-4(6H)-one

There total 4 articles about (S)-2,3,9,9a-tetrahydro-8-(3,4-dimethoxyphenyl)-7-(4-methoxyphenyl)-1H-quinolizin-4(6H)-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: 82.0%

: 1394132-09-2
(S)-4,6,7,8,9,9a-hexahydro-3-(4-methoxyphenyl)-6-oxo-1H-quinolizin-2-yl trifluoromethanesulfonate

: 122775-35-3
3,4-Dimethoxyphenylboronic acid

: 1394132-10-5
(S)-2,3,9,9a-tetrahydro-8-(3,4-dimethoxyphenyl)-7-(4-methoxyphenyl)-1H-quinolizin-4(6H)-one

Guidance literature:: (S)-4,6,7,8,9,9a-hexahydro-3-(4-methoxyphenyl)-6-oxo-1H-quinolizin-2-yl trifluoromethanesulfonate; 3,4-Dimethoxyphenylboronic acid; With sodium carbonate; In 1,4-dioxane; water; for 0.25h; Inert atmosphere;

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; at 85 ℃; for 1.5h; Inert atmosphere;
DOI:10.1039/c2ob25689d

Reference yield:

: 1394132-12-7
methyl 4-((2S,4S,5R)-4-hydroxy-5-(4-methoxyphenyl)piperidin-2-yl)butanoate

: 1394132-10-5
(S)-2,3,9,9a-tetrahydro-8-(3,4-dimethoxyphenyl)-7-(4-methoxyphenyl)-1H-quinolizin-4(6H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / Inert atmosphere; Reflux

2.1: sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine / dichloromethane; dimethyl sulfoxide / 1 h / 0 °C / Inert atmosphere

3.1: potassium hydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

3.2: 0.5 h / 0 - 20 °C / Inert atmosphere

4.1: sodium carbonate / 1,4-dioxane; water / 0.25 h / Inert atmosphere

4.2: 1.5 h / 85 °C / Inert atmosphere

With sulfur trioxide pyridine complex; potassium hydride; sodium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; 4.1: Suzuki coupling;
DOI:10.1039/c2ob25689d

Reference yield:

: 1394132-07-0
(7R,8S,9aS)-hexahydro-8-hydroxy-7-(4-methoxyphenyl)-1H-quinolizin-4(6H)-one

: 1394132-10-5
(S)-2,3,9,9a-tetrahydro-8-(3,4-dimethoxyphenyl)-7-(4-methoxyphenyl)-1H-quinolizin-4(6H)-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine / dichloromethane; dimethyl sulfoxide / 1 h / 0 °C / Inert atmosphere

2.1: potassium hydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

2.2: 0.5 h / 0 - 20 °C / Inert atmosphere

3.1: sodium carbonate / 1,4-dioxane; water / 0.25 h / Inert atmosphere

3.2: 1.5 h / 85 °C / Inert atmosphere

With sulfur trioxide pyridine complex; potassium hydride; sodium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; 3.1: Suzuki coupling;
DOI:10.1039/c2ob25689d