(3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-3′-(4-fluorophenyl)-4′-isopropyl-7′,7′-dimethyl-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]

Base Information

Chemical Name:(3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-3′-(4-fluorophenyl)-4′-isopropyl-7′,7′-dimethyl-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]
CAS No.:1332488-94-4
Molecular Formula:C₃₂H₄₆FNO₂Si
Molecular Weight:523.807
Hs Code.:

(3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-3′-(4-fluorophenyl)-4′-isopropyl-7′,7′-dimethyl-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]

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Chemical Property of (3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-3′-(4-fluorophenyl)-4′-isopropyl-7′,7′-dimethyl-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]

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Technology Process of (3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-3′-(4-fluorophenyl)-4′-isopropyl-7′,7′-dimethyl-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]

There total 13 articles about (3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-3′-(4-fluorophenyl)-4′-isopropyl-7′,7′-dimethyl-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline] 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:

: 1332488-52-4
(3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-3′-(4-fluorophenyl)-2-iodo-4′-isopropyl-7′,7′-dimethyl-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]

: 1332488-94-4
(3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-3′-(4-fluorophenyl)-4′-isopropyl-7′,7′-dimethyl-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]

Guidance literature:: With palladium 10% on activated carbon; hydrogen; triethylamine; In methanol; for 12h; under 7500.75 Torr;
DOI:10.1021/jm500431d

Reference yield:

: 1332487-55-4
(R)-((S)-5-(tert-butyldimethylsilyloxy)-4-cyclopentenyl-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(4-fluorophenyl)methanol

: 1332488-94-4
(3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-3′-(4-fluorophenyl)-4′-isopropyl-7′,7′-dimethyl-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]

Guidance literature:: Multi-step reaction with 2 steps

1: Iodine monochloride / dichloromethane / 24 h / 25 °C

2: triethylamine; palladium 10% on activated carbon; hydrogen / methanol / 12 h / 7500.75 Torr

With palladium 10% on activated carbon; hydrogen; Iodine monochloride; triethylamine; In methanol; dichloromethane;
DOI:10.1021/jm500431d

Reference yield:

: 873-95-0
1-amino-5,5-dimethylcyclohexen-3-one

: 1332488-94-4
(3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-3′-(4-fluorophenyl)-4′-isopropyl-7′,7′-dimethyl-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]

Guidance literature:: Multi-step reaction with 12 steps

1: 0.17 h / 210 °C

2: trichlorophosphate / N,N-dimethyl-formamide / 12 h / 80 °C

3: sodium iodide; acetyl chloride / acetonitrile / 3 h / 50 °C

4: (1R,2S)-1-Amino-2-indanol; borane Ν,Ν-diethylaniline complex / tetrahydrofuran / 28 h / 0 - 20 °C

5: 2,6-dimethylpyridine / tetrahydrofuran / 12 h / 20 °C

6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran; toluene / 12 h / 85 °C / Inert atmosphere

7: diisobutylaluminium hydride / dichloromethane / 2 h / 0 °C

8: Dess-Martin periodane / dichloromethane / 12 h / 0 - 20 °C

9: isopropylmagnesium chloride / tetrahydrofuran / 12 h / -40 - 20 °C

10: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride / tetrahydrofuran / 36 h / 50 °C / Inert atmosphere

11: Iodine monochloride / dichloromethane / 24 h / 25 °C

12: triethylamine; palladium 10% on activated carbon; hydrogen / methanol / 12 h / 7500.75 Torr

With 2,6-dimethylpyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; borane Ν,Ν-diethylaniline complex; palladium 10% on activated carbon; (1R,2S)-1-Amino-2-indanol; hydrogen; isopropylmagnesium chloride; Iodine monochloride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; acetyl chloride; cesium fluoride; sodium iodide; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6: |Negishi Coupling / 10: |Suzuki Coupling;
DOI:10.1021/jm500431d