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

Base Information

• Chemical Name: (R)-((5S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(4-(trifluoromethyl)phenyl)methanol
• CAS No.: 1332486-56-2
• Molecular Formula: C₂₈H₃₉F₃INO₂Si
• Molecular Weight: 633.608

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

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

Chemical Property:

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

There total 28 articles about (R)-((5S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(4-(trifluoromethyl)phenyl)methanol 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: 93.0%

(R)-3-((S)-hydroxy(4-(trifluoromethyl)phenyl)methyl)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol (1332486-57-3) + t-butyldimethylsiyl triflate (69739-34-0) → (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)

Guidance literature:

(R)-3-((S)-hydroxy(4-(trifluoromethyl)phenyl)methyl)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol; With 2,6-dimethylpyridine; In tetrahydrofuran; at -10 ℃;

t-butyldimethylsiyl triflate; In tetrahydrofuran; at -10 - 20 ℃; for 19.5h;

Reference yield: 51.0%

4-Iodobenzotrifluoride (455-13-0) + (S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde (1332486-87-9) → (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) + (S)-((5S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(4-(trifluoromethyl)phenyl)methanol (1332487-04-3)

Guidance literature:

4-Iodobenzotrifluoride; With isopropylmagnesium chloride; In tetrahydrofuran; at -20 ℃; for 5h;

(S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde; In tetrahydrofuran; at -40 - 20 ℃; for 12h;

With methanol; In tetrahydrofuran; at 0 ℃; for 0.5h;

Reference yield:

1-amino-5,5-dimethylcyclohexen-3-one (873-95-0) → (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)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 0.17 h / 210 °C

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

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

4.1: (1R,2S)-1-Amino-2-indanol; borane Ν,Ν-diethylaniline complex / tetrahydrofuran / 28 h / 0 - 20 °C

5.1: 2,6-dimethylpyridine / tetrahydrofuran / 12 h / 0 - 20 °C

6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; tetrahydrofuran / 12 h / 85 °C / Inert atmosphere; Reflux

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

7.2: 0.08 h

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

9.1: isopropylmagnesium chloride / tetrahydrofuran / 5 h / -20 °C

9.2: 12 h / -40 - 20 °C

9.3: 0.5 h / 0 °C

With 2,6-dimethylpyridine; borane Ν,Ν-diethylaniline complex; (1R,2S)-1-Amino-2-indanol; isopropylmagnesium chloride; diisobutylaluminium hydride; Dess-Martin periodane; acetyl chloride; sodium iodide; trichlorophosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;

upstream raw materials:

4-Iodobenzotrifluoride

(S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde

1-amino-5,5-dimethylcyclohexen-3-one

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

Downstream raw materials:

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

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

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

(3′R,9′S)-4′-isopropyl-7′,7′-dimethyl-3′-(4-(trifluoromethyl)phenyl)-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinolin]-9′-ol

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