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

Base Information

Chemical Name:(4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-methanolphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-ol
CAS No.:1393603-43-4
Molecular Formula:C₂₆H₃₅NO₆
Molecular Weight:457.567
Hs Code.:

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

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

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

There total 13 articles about (4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-methanolphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-ol 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: 72.0%

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

: 1393603-43-4
(4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-methanolphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-ol

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1039/c2ob25880c

Reference yield:

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

: 1393603-43-4
(4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-methanolphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-ol

Guidance literature:: Multi-step reaction with 4 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

4: L-Selectride / tetrahydrofuran / 1 h / -78 °C

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

Reference yield:

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

: 1393603-43-4
(4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-methanolphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-ol

Guidance literature:: Multi-step reaction with 10 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

10.1: L-Selectride / tetrahydrofuran / 1 h / -78 °C

With phosgene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; L-Selectride; 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