(1S,9S,9aS)-1-benzoyloxy-9-diphenyl(methyl)silyloxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one

Base Information

Chemical Name:(1S,9S,9aS)-1-benzoyloxy-9-diphenyl(methyl)silyloxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one
CAS No.:1273550-88-1
Molecular Formula:C₂₉H₃₁NO₄Si
Molecular Weight:485.655
Hs Code.:

Synonyms:(1S,9S,9aS)-1-benzoyloxy-9-diphenyl(methyl)silyloxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one

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Chemical Property of (1S,9S,9aS)-1-benzoyloxy-9-diphenyl(methyl)silyloxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one

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Technology Process of (1S,9S,9aS)-1-benzoyloxy-9-diphenyl(methyl)silyloxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one

There total 9 articles about (1S,9S,9aS)-1-benzoyloxy-9-diphenyl(methyl)silyloxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-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: 9.0%

: 1273550-87-0
(5S)-5-benzoyloxy-1-[4-oxo-4-(diphenyl(methyl)silyl)butyl]-6-(phenylsulfenyl)piperidin-2-one

: (1S,9R,9aS)-1-benzoyloxy-9-diphenyl(methyl)silyloxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one

: 1273550-88-1
(1S,9S,9aS)-1-benzoyloxy-9-diphenyl(methyl)silyloxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one

: 1273550-89-2
(-)-(S)-5-benzoyloxy-1-[4-oxo-4-(diphenyl(methyl)silyl)butyl]piperidin-2-one

Guidance literature:: With tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile); In toluene; for 7h; optical yield given as %de; Inert atmosphere; Reflux;
DOI:10.1016/j.tet.2010.12.048

Reference yield:

: C₂₇H₃₁NS₂Si

: (1S,9R,9aS)-1-benzoyloxy-9-diphenyl(methyl)silyloxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one

: 1273550-88-1
(1S,9S,9aS)-1-benzoyloxy-9-diphenyl(methyl)silyloxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one

: 1273550-89-2
(-)-(S)-5-benzoyloxy-1-[4-oxo-4-(diphenyl(methyl)silyl)butyl]piperidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: phenylhydrazine / ethanol / 3.5 h / 20 °C / Inert atmosphere

2.1: triethylamine / tetrahydrofuran / 3.67 h / 20 °C / Inert atmosphere; Cooling with ice

3.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / -40 °C / Inert atmosphere; Cooling with acetone-dry ice

3.2: -40 °C / Inert atmosphere

4.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 0.37 h / Inert atmosphere; Cooling with CCl₄-dry ice

5.1: toluene-4-sulfonic acid / dichloromethane; water / 20 °C / Inert atmosphere

6.1: dmap; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

7.1: water; sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene / acetonitrile / 0.38 h / 20 °C / Inert atmosphere

8.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / toluene / 7 h / Inert atmosphere; Reflux

With dmap; sodium tetrahydroborate; potassium tert-butylate; water; tri-n-butyl-tin hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; phenylhydrazine; bis-[(trifluoroacetoxy)iodo]benzene; 1,1'-azobis(1-cyanocyclohexanenitrile); In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; acetonitrile;
DOI:10.1016/j.tet.2010.12.048

Reference yield:

: C₂₅H₃₅NO₃S₂Si

: (1S,9R,9aS)-1-benzoyloxy-9-diphenyl(methyl)silyloxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one

: 1273550-88-1
(1S,9S,9aS)-1-benzoyloxy-9-diphenyl(methyl)silyloxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one

: 1273550-89-2
(-)-(S)-5-benzoyloxy-1-[4-oxo-4-(diphenyl(methyl)silyl)butyl]piperidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid / dichloromethane; water / 20 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

3: water; sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene / acetonitrile / 0.38 h / 20 °C / Inert atmosphere

4: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / toluene / 7 h / Inert atmosphere; Reflux

With dmap; water; tri-n-butyl-tin hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; 1,1'-azobis(1-cyanocyclohexanenitrile); In dichloromethane; water; toluene; acetonitrile;
DOI:10.1016/j.tet.2010.12.048