(4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-one

Base Information

Chemical Name:(4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-one
CAS No.:1393603-37-6
Molecular Formula:C₂₆H₃₁NO₆
Molecular Weight:453.535
Hs Code.:

Synonyms:(4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-one

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Chemical Property of (4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-one

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Technology Process of (4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-one

There total 11 articles about (4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(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: 80.0%

: 1248344-23-1
4-(methoxymethoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

: 1393603-26-3
C₁₇H₂₂INO₃

: 1393603-37-6
(4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-one

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride; In 1,2-dimethoxyethane; at 95 ℃; for 18h; Inert atmosphere;
DOI:10.1039/c2ob25880c

Reference yield:

: 60032-63-5
4-hydroxy-3-iodo-benzaldehyde

: 1393603-37-6
(4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-one

Guidance literature:: Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C / Cooling with ice

2: potassium acetate; palladium diacetate / N,N-dimethyl-formamide / 60 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride / 1,2-dimethoxyethane / 18 h / 95 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; palladium diacetate; N-ethyl-N,N-diisopropylamine; cesium fluoride; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/c2ob25880c

Reference yield:

: 1484-84-0
2(RS)-(2-hydroxyethyl)piperidine

: 1393603-37-6
(4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: ethanol / Resolution of racemate; Cooling

2.1: triethylamine / dichloromethane / 20 °C

3.1: phosgene; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

3.2: 4 h / 20 °C / Inert atmosphere

4.1: tetrahydrofuran; diethyl ether / 4.5 h / -78 - 20 °C / Inert atmosphere

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C

6.1: sodium hydroxide / methanol / 16 h / 55 °C

7.1: trifluoroacetic acid / dichloromethane / 1 h / 0 °C

8.1: sodium hydroxide / tetrahydrofuran / 4 h / 0 - 20 °C

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride / 1,2-dimethoxyethane / 18 h / 95 °C / Inert atmosphere

With phosgene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; cesium fluoride; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; 3.1: Swern oxidation / 3.2: Swern oxidation;
DOI:10.1039/c2ob25880c