(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

Base Information

Chemical Name:(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
CAS No.:1332485-18-3
Molecular Formula:C₂₇H₃₂F₃NO₃
Molecular Weight:475.551
Hs Code.:

Synonyms:(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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (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

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Technology Process of (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

There total 28 articles about (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 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: 91.0%

: 1332489-18-5
(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]

: 1332485-18-3
(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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 17h;

Reference yield:

: 1332489-18-5
(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]

: 1332485-18-3
(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

: (3S,9R)-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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 12h; enantioselective reaction;
DOI:10.1021/jm500431d

Reference yield:

: 1332486-56-2
(R)-((5S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(4-(trifluoromethyl)phenyl)methanol

: 1332485-18-3
(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

Guidance literature:: Multi-step reaction with 4 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

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

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 17 h / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; iodine; lithium carbonate; triethylamine; cesium fluoride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile;