(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]

Base Information

• Chemical Name: (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]
• CAS No.: 1332489-18-5
• Molecular Formula: C₃₃H₄₆F₃NO₃Si
• Molecular Weight: 589.814
• Mol file: 1332489-18-5.mol

Synonyms:(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]

Chemical Property of (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]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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]

There total 23 articles about (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] 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: 81.0%

(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) → (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] (1332489-18-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; triethylamine; In methanol; at 20 ℃; for 2.5h; under 2585.81 Torr;

Reference yield:

(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]-3-ol hydrochloride → (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] (1332489-18-5) + (3S,9S)-9-((tert-butyldimethylsilyl)oxy)-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]

Guidance literature:

With triethylsilane; titanium tetrachloride; In dichloromethane; for 6h; Reagent/catalyst; Time; Temperature;

DOI:10.1021/ol501833g

Reference yield:

(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)-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] (1332489-18-5)

Guidance literature:

Multi-step reaction with 2 steps

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

2: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 2.5 h / 20 °C / 2585.81 Torr

With palladium 10% on activated carbon; hydrogen; iodine; lithium carbonate; triethylamine; In tetrahydrofuran; methanol; 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

(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]

(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

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)-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