(3′R,6′S,9′S)-9′-(tert-butyldimethylsilyloxy)-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]-6′-yl acetate

Base Information

Chemical Name:(3′R,6′S,9′S)-9′-(tert-butyldimethylsilyloxy)-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]-6′-yl acetate
CAS No.:1332490-86-4
Molecular Formula:C₃₅H₄₈F₃NO₄Si
Molecular Weight:631.851
Hs Code.:

(3′R,6′S,9′S)-9′-(tert-butyldimethylsilyloxy)-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]-6′-yl acetate

Synonyms:(3′R,6′S,9′S)-9′-(tert-butyldimethylsilyloxy)-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]-6′-yl acetate

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Chemical Property of (3′R,6′S,9′S)-9′-(tert-butyldimethylsilyloxy)-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]-6′-yl acetate

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Technology Process of (3′R,6′S,9′S)-9′-(tert-butyldimethylsilyloxy)-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]-6′-yl acetate

There total 18 articles about (3′R,6′S,9′S)-9′-(tert-butyldimethylsilyloxy)-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]-6′-yl acetate 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: 52.0%

: 1332490-87-5
(3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-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]5′-oxide

: 108-24-7
acetic anhydride

: 1332490-85-3
(3′R,6′R,9′S)-9′-(tert-butyldimethylsilyloxy)-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]-6′-yl acetate

: 1332490-86-4
(3′R,6′S,9′S)-9′-(tert-butyldimethylsilyloxy)-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]-6′-yl acetate

Guidance literature:: (3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-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]5′-oxide; acetic anhydride; at 130 ℃; for 2h;

With sodium hydrogencarbonate; In diethyl ether; water;

Reference yield:

: 1332486-49-3
(S)-ethyl 5-(tert-butyldimethylsilyloxy)-2,4-diiodo-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carboxylate

: 1332490-85-3
(3′R,6′R,9′S)-9′-(tert-butyldimethylsilyloxy)-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]-6′-yl acetate

: 1332490-86-4
(3′R,6′S,9′S)-9′-(tert-butyldimethylsilyloxy)-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]-6′-yl acetate

Guidance literature:: Multi-step reaction with 9 steps

1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; tetrahydrofuran / 12 h / 85 °C / Inert atmosphere; Reflux

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

2.2: 0.08 h

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

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

4.2: 12 h / -40 - 20 °C

4.3: 0.5 h / 0 °C

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

6.1: Iodine monochloride / dichloromethane / 24 h

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

8.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 18 h

9.1: 2 h / 130 °C

With hydrogen; isopropylmagnesium chloride; Iodine monochloride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; cesium fluoride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; In tetrahydrofuran; methanol; dichloromethane; chloroform; toluene;

Reference yield:

: 930-29-0
1-chlorocyclopent-1-ene

: 1332490-85-3
(3′R,6′R,9′S)-9′-(tert-butyldimethylsilyloxy)-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]-6′-yl acetate

: 1332490-86-4
(3′R,6′S,9′S)-9′-(tert-butyldimethylsilyloxy)-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]-6′-yl acetate

Guidance literature:: Multi-step reaction with 6 steps

1: potassium acetate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 3 h / 110 °C / Inert atmosphere

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

3: Iodine monochloride / dichloromethane / 24 h

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

5: 3-chloro-benzenecarboperoxoic acid / chloroform / 18 h

6: 2 h / 130 °C

With hydrogen; potassium acetate; Iodine monochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; cesium fluoride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform;