(S)-10',10'-dimethyl-3'-(triisopropylsilyl)-7',8',11',11a'-tetrahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)-dione

Base Information

Chemical Name:(S)-10',10'-dimethyl-3'-(triisopropylsilyl)-7',8',11',11a'-tetrahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)-dione
CAS No.:1447811-54-2
Molecular Formula:C₂₆H₄₁NO₄Si
Molecular Weight:459.701
Hs Code.:

Synonyms:(S)-10',10'-dimethyl-3'-(triisopropylsilyl)-7',8',11',11a'-tetrahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)-dione

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Chemical Property of (S)-10',10'-dimethyl-3'-(triisopropylsilyl)-7',8',11',11a'-tetrahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)-dione

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Technology Process of (S)-10',10'-dimethyl-3'-(triisopropylsilyl)-7',8',11',11a'-tetrahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)-dione

There total 1 articles about (S)-10',10'-dimethyl-3'-(triisopropylsilyl)-7',8',11',11a'-tetrahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)-dione 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:

: 562-13-0
2,2-dimethyl-1,3-cyclohexanedione

: 1447811-54-2
(S)-10',10'-dimethyl-3'-(triisopropylsilyl)-7',8',11',11a'-tetrahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)-dione

Guidance literature:: Multi-step reaction with 6 steps

1.1: camphor-10-sulfonic acid; orthoformic acid triethyl ester / dichloromethane / 72 h / 0 °C / Inert atmosphere

2.1: sodium hydride / mineral oil; tetrahydrofuran / 16 h / Inert atmosphere; Reflux

2.2: 0 °C

3.1: sodium hydride / mineral oil; diethyl ether / 1.5 h / 0 °C / Inert atmosphere

3.2: 6.5 h / 0 °C / Inert atmosphere

4.1: copper(l) cyanide / diethyl ether / 0.17 h / -50 °C / Inert atmosphere

4.2: 16 h / -35 - 20 °C / Inert atmosphere

5.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

5.2: 1 h / -78 °C / Inert atmosphere

5.3: 21 h / -78 - 20 °C / Inert atmosphere

6.1: caesium carbonate / methanol; tetrahydrofuran / 16 h / 65 °C / Inert atmosphere

6.2: 0.33 h / 0 °C / Inert atmosphere

With n-butyllithium; camphor-10-sulfonic acid; copper(l) cyanide; sodium hydride; caesium carbonate; diisopropylamine; orthoformic acid triethyl ester; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; mineral oil;
DOI:10.1021/ja405547f

Reference yield:

: 1447811-54-2
(S)-10',10'-dimethyl-3'-(triisopropylsilyl)-7',8',11',11a'-tetrahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)-dione

: 1447811-56-4
(4'R,11a'S)-4'-((dimethyl(phenyl)silyl)methyl)-10',10'-dimethyl-3',4',7',8',11',11a'-hexahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)dione

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetrabutyl ammonium fluoride / 1,4-dioxane / 0.47 h / 100 °C / Inert atmosphere

2.1: magnesium / tetrahydrofuran; ethylene dibromide / 2.5 h / Inert atmosphere; Reflux

2.2: 16.75 h / -78 - 20 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; magnesium; In tetrahydrofuran; 1,4-dioxane; ethylene dibromide;
DOI:10.1021/ja405547f

Reference yield:

: 1447811-54-2
(S)-10',10'-dimethyl-3'-(triisopropylsilyl)-7',8',11',11a'-tetrahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)-dione

: 1447811-58-6
(2'S,4'R,11a'S)-4'-((dimethyl(phenyl)silyl)methyl)-2'-hydroxy-10',10'-dimethyl-1',2',3',4',7',8',11',11a'-octahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinolin]-6'(10'H)-one

: (2'R,4'R,11a'S)-4'-((dimethyl(phenyl)silyl)methyl)-2'-hydroxy-10',10'-dimethyl-1',2',3',4',7',8',11',11a'-octahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinolin]-6'(10'H)-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrabutyl ammonium fluoride / 1,4-dioxane / 0.47 h / 100 °C / Inert atmosphere

2.1: magnesium / tetrahydrofuran; ethylene dibromide / 2.5 h / Inert atmosphere; Reflux

2.2: 16.75 h / -78 - 20 °C / Inert atmosphere

3.1: L-Selectride / tetrahydrofuran / 16 h / -78 - 20 °C / Inert atmosphere

3.2: 0.33 h / Inert atmosphere

With tetrabutyl ammonium fluoride; L-Selectride; magnesium; In tetrahydrofuran; 1,4-dioxane; ethylene dibromide;
DOI:10.1021/ja405547f