(-)-(5S)-4-(4,4-difluorocyclohexyl)-2-[1-(5-{[(2S)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol

Base Information

• Chemical Name: (-)-(5S)-4-(4,4-difluorocyclohexyl)-2-[1-(5-{[(2S)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol
• CAS No.: 1354495-43-4
• Molecular Formula: C₃₇H₄₄F₆N₄O₄
• Molecular Weight: 722.771

Synonyms:(-)-(5S)-4-(4,4-difluorocyclohexyl)-2-[1-(5-{[(2S)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol

Chemical Property of (-)-(5S)-4-(4,4-difluorocyclohexyl)-2-[1-(5-{[(2S)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(5S)-4-(4,4-difluorocyclohexyl)-2-[1-(5-{[(2S)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol

There total 21 articles about (-)-(5S)-4-(4,4-difluorocyclohexyl)-2-[1-(5-{[(2S)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-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: 94.0%

(5S)-4-(4,4-difluorocyclohexyl)-2-[1-(5-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol (1354495-44-5) → (-)-(5S)-4-(4,4-difluorocyclohexyl)-2-[1-(5-{[(2S)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol (1354495-43-4)

Guidance literature:

With hydrogenchloride; water; In methanol; at 50 ℃; for 2.5h;

Reference yield:

4,4-difluorocyclohexane carboxyaldehyde (265108-36-9) → (-)-(5S)-4-(4,4-difluorocyclohexyl)-2-[1-(5-{[(2S)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol (1354495-43-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: toluene / 0.17 h / 100 °C

1.2: 15 h / Reflux

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C

3.1: diisobutylaluminium hydride / toluene / 2 h / -50 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / Cooling with ice

4.2: 3.5 h / 20 °C / Cooling with ice

5.1: magnesium / tetrahydrofuran

5.2: 2.3 h / 20 °C / Cooling with ice

6.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 6.3 h / Cooling with acetone-dry ice

7.1: zinc dibromide / dichloromethane / 68.5 h / 30 °C

8.1: CHIRALPAK? AD-H / hexane; isopropyl alcohol

9.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 3 h / 80 °C

10.1: johnphos; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 0.83 h / 60 °C / Microwave irradiation

11.1: hydrogenchloride; water / methanol; 1,4-dioxane / 1.5 h / 70 °C

12.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 2 h / 70 °C

13.1: hydrogenchloride / methanol; water / 2 h / 60 °C

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; water; sodium hydride; diisobutylaluminium hydride; caesium carbonate; magnesium; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc dibromide; (bis-(2-methoxyethyl)amino)sulfur trufluoride; johnphos; sodium t-butanolate; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; mineral oil;

Reference yield:

1-tert-butoxycarbonyl-4-cyanopiperidine (91419-52-2) → (-)-(5S)-4-(4,4-difluorocyclohexyl)-2-[1-(5-{[(2S)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol (1354495-43-4)

Guidance literature:

Multi-step reaction with 14 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; ethylbenzene; n-heptane / 3 h / Cooling with acetone-dry ice

1.2: 24 h / 20 °C / Cooling with acetone-dry ice

2.1: toluene / 0.17 h / 100 °C

2.2: 15 h / Reflux

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C

4.1: diisobutylaluminium hydride / toluene / 2 h / -50 °C

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / Cooling with ice

5.2: 3.5 h / 20 °C / Cooling with ice

6.1: magnesium / tetrahydrofuran

6.2: 2.3 h / 20 °C / Cooling with ice

7.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 6.3 h / Cooling with acetone-dry ice

8.1: zinc dibromide / dichloromethane / 68.5 h / 30 °C

9.1: CHIRALPAK? AD-H / hexane; isopropyl alcohol

10.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 3 h / 80 °C

11.1: johnphos; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 0.83 h / 60 °C / Microwave irradiation

12.1: hydrogenchloride; water / methanol; 1,4-dioxane / 1.5 h / 70 °C

13.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 2 h / 70 °C

14.1: hydrogenchloride / methanol; water / 2 h / 60 °C

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; water; sodium hydride; diisobutylaluminium hydride; caesium carbonate; magnesium; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc dibromide; (bis-(2-methoxyethyl)amino)sulfur trufluoride; johnphos; sodium t-butanolate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; hexane; n-heptane; dichloromethane; ethylbenzene; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; mineral oil;

upstream raw materials:

(5S)-2-[1-(5-bromopyrimidin-2-yl)piperidin-4-yl]-4-(4,4-difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-5,6,7,8-tetrahydroquinoline

(5S)-4-(4,4-difluorocyclohexyl)-2-[1-(5-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol

(-)-(5S)-4-(4,4-difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-{1-[5-(morpholin-4-yl)pyrimidin-2-yl]piperidin-4-yl}-5,6,7,8-tetrahydroquinoline

ethyl 4,4-difluorocyclohexane-1-carboxylate

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