(S)-10',10'-dimethyl-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-7',8',11',11a'-tetrahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)-dione
• CAS No.: 1447811-55-3
• Molecular Formula: C₁₇H₂₁NO₄
• Molecular Weight: 303.358

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (S)-10',10'-dimethyl-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-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:

2,2-dimethyl-1,3-cyclohexanedione (562-13-0) → (S)-10',10'-dimethyl-7',8',11',11a'-tetrahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)-dione (1447811-55-3)

Guidance literature:

Multi-step reaction with 7 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

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

With n-butyllithium; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; copper(l) cyanide; sodium hydride; caesium carbonate; diisopropylamine; orthoformic acid triethyl ester; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; mineral oil;

DOI:10.1021/ja405547f

Reference yield: 100.0%

(S)-10',10'-dimethyl-7',8',11',11a'-tetrahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)-dione (1447811-55-3) + chloromethyldimethylphenylsilane (1833-51-8) → (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 (1447811-56-4)

Guidance literature:

chloromethyldimethylphenylsilane; With magnesium; In tetrahydrofuran; ethylene dibromide; for 2.5h; Inert atmosphere; Reflux;

(S)-10',10'-dimethyl-7',8',11',11a'-tetrahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)-dione; With copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 16.75h; Inert atmosphere;

DOI:10.1021/ja405547f

Reference yield:

(S)-10',10'-dimethyl-7',8',11',11a'-tetrahydrospiro[[1,3]dioxolane-2,9'-pyrido[1,2-b]isoquinoline]-2',6'(1'H,10'H)-dione (1447811-55-3) → (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 (1447811-58-6) + (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 2 steps

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

1.2: 16.75 h / -78 - 20 °C / Inert atmosphere

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

2.2: 0.33 h / Inert atmosphere

With L-Selectride; magnesium; In tetrahydrofuran; ethylene dibromide;

DOI:10.1021/ja405547f

upstream raw materials:

2,2-dimethyl-1,3-cyclohexanedione

Downstream raw materials:

(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

(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

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