(3R,9S)-9-(tert-butyldimethylsilyloxy)-3’-iodo-4-isopropyl-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2’,3’,5’,6,6’,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4’-pyran]

Base Information

• Chemical Name: (3R,9S)-9-(tert-butyldimethylsilyloxy)-3’-iodo-4-isopropyl-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2’,3’,5’,6,6’,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4’-pyran]
• CAS No.: 1332489-19-6
• Molecular Formula: C₃₃H₄₅F₃INO₃Si
• Molecular Weight: 715.71
• Mol file: 1332489-19-6.mol

Synonyms:(3R,9S)-9-(tert-butyldimethylsilyloxy)-3’-iodo-4-isopropyl-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2’,3’,5’,6,6’,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4’-pyran]

Chemical Property of (3R,9S)-9-(tert-butyldimethylsilyloxy)-3’-iodo-4-isopropyl-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2’,3’,5’,6,6’,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4’-pyran]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,9S)-9-(tert-butyldimethylsilyloxy)-3’-iodo-4-isopropyl-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2’,3’,5’,6,6’,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4’-pyran]

There total 21 articles about (3R,9S)-9-(tert-butyldimethylsilyloxy)-3’-iodo-4-isopropyl-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2’,3’,5’,6,6’,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4’-pyran] 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: 70.0%

(R)-((S)-5-(tert-butyldimethylsilyloxy)-4-(3,6-dihydro-2H-pyran-4-yl)-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(4-(trifluoromethyl)phenyl)methanol (1332487-79-2) → (3R,9S)-9-(tert-butyldimethylsilyloxy)-3’-iodo-4-isopropyl-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2’,3’,5’,6,6’,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4’-pyran] (1332489-19-6)

Guidance literature:

(R)-((S)-5-(tert-butyldimethylsilyloxy)-4-(3,6-dihydro-2H-pyran-4-yl)-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(4-(trifluoromethyl)phenyl)methanol; With lithium carbonate; In tetrahydrofuran; acetonitrile; for 0.166667h;

With iodine; In tetrahydrofuran; acetonitrile; at 50 ℃; for 70h;

Reference yield:

(R)-((5S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(4-(trifluoromethyl)phenyl)methanol (1332486-56-2) → (3R,9S)-9-(tert-butyldimethylsilyloxy)-3’-iodo-4-isopropyl-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2’,3’,5’,6,6’,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4’-pyran] (1332489-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: cesium fluoride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran; N,N-dimethyl-formamide / 5.5 h / 50 °C

2: iodine; lithium carbonate / tetrahydrofuran; acetonitrile / 118.5 h / 50 - 70 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; iodine; lithium carbonate; cesium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

ethyl 2,4-dihydroxy-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate (1332486-06-2) → (3R,9S)-9-(tert-butyldimethylsilyloxy)-3’-iodo-4-isopropyl-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2’,3’,5’,6,6’,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4’-pyran] (1332489-19-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: triethylamine / dichloromethane / 20 h / 20 °C

2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 20.5 h / 20 °C

3.1: trichlorophosphate / tetrahydrofuran; N,N-dimethyl-formamide / 70 h / 60 - 70 °C

4.1: sodium iodide; acetyl chloride / acetonitrile / 17 h / 20 °C

5.1: borane N,N-diethylaniline complex; (1R,2S)-1-Amino-2-indanol / tetrahydrofuran / 22 h / 0 - 20 °C

6.1: diisobutylaluminium hydride / dichloromethane / 66 h / 0 - 20 °C

6.2: 1 h / 0 °C

7.1: sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / toluene / 65 h / 40 °C

8.1: magnesium; iodine / tetrahydrofuran / 2.5 h / 35 °C

8.2: 1.17 h / -80 - -40 °C

9.1: 2,6-dimethylpyridine / tetrahydrofuran / 19.5 h / -10 - 20 °C

10.1: cesium fluoride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran; N,N-dimethyl-formamide / 5.5 h / 50 °C

11.1: iodine; lithium carbonate / tetrahydrofuran; acetonitrile / 118.5 h / 50 - 70 °C

With 2,6-dimethylpyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; borane N,N-diethylaniline complex; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (1R,2S)-1-Amino-2-indanol; iodine; lithium carbonate; diisobutylaluminium hydride; sodium hydrogencarbonate; magnesium; triethylamine; acetyl chloride; cesium fluoride; sodium iodide; trichlorophosphate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

(R)-((S)-5-(tert-butyldimethylsilyloxy)-4-(3,6-dihydro-2H-pyran-4-yl)-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(4-(trifluoromethyl)phenyl)methanol

(R)-((5S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(4-(trifluoromethyl)phenyl)methanol

(R)-3-((S)-hydroxy(4-(trifluoromethyl)phenyl)methyl)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol

ethyl 4-hydroxy-2-isopropyl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate

Downstream raw materials:

(3R,9S)-4-isopropyl-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2’,3’,5’,6,6’,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4’-pyran]-9-ol

(3R,9S)-9-(tert-butyldimethylsilyloxy)-4-isopropyl-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2′,3′,5′,6,6′,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4′-pyran]

(3R,9S)-4-isopropyl-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2’,3’,5’,6,6’,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-9-ol hydrocholride

(3R,9S)-4-isopropyl-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2’,3’,5’,6,6’,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4’-pyran]-9-ol hydrobromide