(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

Base Information

• Chemical Name: (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
• CAS No.: 1447811-58-6
• Molecular Formula: C₂₆H₃₇NO₄Si
• Molecular Weight: 455.67

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 12 articles about (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 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: 71.0%

(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) → (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:

(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; With L-Selectride; In tetrahydrofuran; at -78 - 20 ℃; for 16h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; for 0.333333h; Inert atmosphere;

DOI:10.1021/ja405547f

Reference yield: 71.0%

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 → (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:

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; With L-Selectride; In tetrahydrofuran; at -78 - 20 ℃; for 16h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1021/ja5074646

Reference yield:

2,2-dimethyl-1,3-cyclohexanedione (562-13-0) → (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 9 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

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

8.2: 16.75 h / -78 - 20 °C / Inert atmosphere

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

9.2: 0.33 h / Inert atmosphere

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

DOI:10.1021/ja405547f

upstream raw materials:

(S)-(1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl 2-((8-(methoxycarbonyl)-6,6-dimethyl-1,4-dioxaspiro[4.5]dec-7-en-7-yl)methyl)-4-oxo-5-(triisopropylsilyl)-3,4-dihydropyridine-1(2H)-carboxylate

(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

(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

(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

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