(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]

Base Information

Chemical Name:(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]
CAS No.:1332488-52-4
Molecular Formula:C₃₂H₄₅FINO₂Si
Molecular Weight:649.703
Hs Code.:

(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]

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Chemical Property of (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]

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Technology Process of (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]

There total 12 articles about (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] 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:

: 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

: 1332488-52-4
(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]

Guidance literature:: With Iodine monochloride; In dichloromethane; at 25 ℃; for 24h;
DOI:10.1021/jm500431d

Reference yield:

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

: 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]

Guidance literature:: Multi-step reaction with 11 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

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

Reference yield:

: 1332486-06-2
ethyl 2,4-dihydroxy-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate

: 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]

Guidance literature:: Multi-step reaction with 10 steps

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

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

3: (1R,2S)-1-Amino-2-indanol; borane Ν,Ν-diethylaniline complex / tetrahydrofuran / 28 h / 0 - 20 °C

4: 2,6-dimethylpyridine / tetrahydrofuran / 12 h / 20 °C

5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran; toluene / 12 h / 85 °C / Inert atmosphere

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

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

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

9: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride / tetrahydrofuran / 36 h / 50 °C / Inert atmosphere

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

With 2,6-dimethylpyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; borane Ν,Ν-diethylaniline complex; (1R,2S)-1-Amino-2-indanol; isopropylmagnesium chloride; Iodine monochloride; diisobutylaluminium hydride; Dess-Martin periodane; acetyl chloride; cesium fluoride; sodium iodide; trichlorophosphate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 5: |Negishi Coupling / 9: |Suzuki Coupling;
DOI:10.1021/jm500431d