(4S,9aS)-hexahydro-4-(2-(2'-tert-butyldimethylsiloxy-5'-carboxaldehyphenyl)-4,5dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate

Base Information

Chemical Name:(4S,9aS)-hexahydro-4-(2-(2'-tert-butyldimethylsiloxy-5'-carboxaldehyphenyl)-4,5dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate
CAS No.:1393603-58-1
Molecular Formula:C₃₃H₄₅NO₆Si
Molecular Weight:579.809
Hs Code.:

Synonyms:(4S,9aS)-hexahydro-4-(2-(2'-tert-butyldimethylsiloxy-5'-carboxaldehyphenyl)-4,5dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate

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Chemical Property of (4S,9aS)-hexahydro-4-(2-(2'-tert-butyldimethylsiloxy-5'-carboxaldehyphenyl)-4,5dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate

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Technology Process of (4S,9aS)-hexahydro-4-(2-(2'-tert-butyldimethylsiloxy-5'-carboxaldehyphenyl)-4,5dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate

There total 18 articles about (4S,9aS)-hexahydro-4-(2-(2'-tert-butyldimethylsiloxy-5'-carboxaldehyphenyl)-4,5dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate 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: 83.0%

: 1393603-56-9
(4S,9aS)-hexahydro-4-(2-(2'-hydroxy-5'-carboxaldehyphenyl)-4,5-dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1393603-58-1
(4S,9aS)-hexahydro-4-(2-(2'-tert-butyldimethylsiloxy-5'-carboxaldehyphenyl)-4,5dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h;
DOI:10.1039/c2ob25880c

Reference yield:

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

: 1393603-58-1
(4S,9aS)-hexahydro-4-(2-(2'-tert-butyldimethylsiloxy-5'-carboxaldehyphenyl)-4,5dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate

Guidance literature:: Multi-step reaction with 8 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

5: manganese(IV) oxide / diethyl ether; acetone / 0.33 h

6: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

7: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C

8: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

With dmap; manganese(IV) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; palladium diacetate; L-Selectride; triethylamine; N-ethyl-N,N-diisopropylamine; cesium fluoride; trifluoroacetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1039/c2ob25880c

Reference yield:

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

: 1393603-58-1
(4S,9aS)-hexahydro-4-(2-(2'-tert-butyldimethylsiloxy-5'-carboxaldehyphenyl)-4,5dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate

Guidance literature:: Multi-step reaction with 15 steps

1.1: tetrahydrofuran; methanol / 0.5 h / 35 - 55 °C / Resolution of racemate

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: sodium hydroxide / methanol; water / 72 h / 20 °C

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

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

12.1: manganese(IV) oxide / diethyl ether; acetone / 0.33 h

13.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

14.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C

15.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

With phosgene; dmap; manganese(IV) oxide; 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; dichloromethane; water; acetone; 3.1: Swern oxidation / 3.2: Swern oxidation;
DOI:10.1039/c2ob25880c