4-((1R,2S)-2-{2-[2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine-1-carbonitrile

Base Information

• Chemical Name: 4-((1R,2S)-2-{2-[2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine-1-carbonitrile
• CAS No.: 1402555-34-3
• Molecular Formula: C₁₈H₂₃FN₂O₃S
• Molecular Weight: 366.457

Synonyms:4-((1R,2S)-2-{2-[2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine-1-carbonitrile

Chemical Property of 4-((1R,2S)-2-{2-[2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine-1-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 4-((1R,2S)-2-{2-[2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine-1-carbonitrile

There total 10 articles about 4-((1R,2S)-2-{2-[2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine-1-carbonitrile 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:

4-ethynyl-piperidine-1-carboxylic acid tert-butyl ester (287192-97-6) → 4-((1R,2S)-2-{2-[2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine-1-carbonitrile (1402555-34-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.08 h / -78 °C

1.2: 1 h / -78 °C

2.1: hydrogen; quinoline / Lindlars catalyst / ethyl acetate / 0.67 h

3.1: diethylzinc / dichloromethane; diethyl ether / 0.17 h / -20 °C / Inert atmosphere

3.2: 0.17 h

3.3: 24 h / 0 °C

4.1: hydrogen / palladium(II) hydroxide / ethyl acetate; ethanol / 2585.81 Torr

4.2: 0 °C

4.3: 0.5 h / 20 °C

5.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C

6.1: triethylamine / dichloromethane / 20 °C

7.1: triethylamine / ethyl acetate / 4 h / Reflux

8.1: sodium hydrogencarbonate; dipotassium hydrogenphosphate / water; dimethyl sulfoxide; methanol / 7 h / 0 - 25 °C / pH 7 - 8

9.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

10.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 20 °C

10.2: 21 h / 20 - 50 °C

11.1: hydrogen / palladium 10% on activated carbon / chloroform / 64 h / 760.05 Torr

12.1: potassium carbonate / chloroform

12.2: 20 °C / Reflux

With quinoline; hydrogenchloride; dmap; dipotassium hydrogenphosphate; n-butyllithium; hydrogen; diethylzinc; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; palladium 10% on activated carbon; palladium(II) hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

Reference yield:

tert-butyl 4-[(4R)-5-(benzyloxy)-4-hydroxypent-1-yn-1-yl]piperidine-1-carboxylate (1192063-78-7) → 4-((1R,2S)-2-{2-[2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine-1-carbonitrile (1402555-34-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: hydrogen; quinoline / Lindlars catalyst / ethyl acetate / 0.67 h

2.1: diethylzinc / dichloromethane; diethyl ether / 0.17 h / -20 °C / Inert atmosphere

2.2: 0.17 h

2.3: 24 h / 0 °C

3.1: hydrogen / palladium(II) hydroxide / ethyl acetate; ethanol / 2585.81 Torr

3.2: 0 °C

3.3: 0.5 h / 20 °C

4.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C

5.1: triethylamine / dichloromethane / 20 °C

6.1: triethylamine / ethyl acetate / 4 h / Reflux

7.1: sodium hydrogencarbonate; dipotassium hydrogenphosphate / water; dimethyl sulfoxide; methanol / 7 h / 0 - 25 °C / pH 7 - 8

8.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

9.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 20 °C

9.2: 21 h / 20 - 50 °C

10.1: hydrogen / palladium 10% on activated carbon / chloroform / 64 h / 760.05 Torr

11.1: potassium carbonate / chloroform

11.2: 20 °C / Reflux

With quinoline; hydrogenchloride; dmap; dipotassium hydrogenphosphate; hydrogen; diethylzinc; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; palladium 10% on activated carbon; palladium(II) hydroxide; In 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

Reference yield:

tert-butyl 4-[(1Z,4R)-5-(benzyloxy)-4-hydroxypent-1-en-1-yl]piperidine-1-carboxylate → 4-((1R,2S)-2-{2-[2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine-1-carbonitrile (1402555-34-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: diethylzinc / dichloromethane; diethyl ether / 0.17 h / -20 °C / Inert atmosphere

1.2: 0.17 h

1.3: 24 h / 0 °C

2.1: hydrogen / palladium(II) hydroxide / ethyl acetate; ethanol / 2585.81 Torr

2.2: 0 °C

2.3: 0.5 h / 20 °C

3.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C

4.1: triethylamine / dichloromethane / 20 °C

5.1: triethylamine / ethyl acetate / 4 h / Reflux

6.1: sodium hydrogencarbonate; dipotassium hydrogenphosphate / water; dimethyl sulfoxide; methanol / 7 h / 0 - 25 °C / pH 7 - 8

7.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

8.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 20 °C

8.2: 21 h / 20 - 50 °C

9.1: hydrogen / palladium 10% on activated carbon / chloroform / 64 h / 760.05 Torr

10.1: potassium carbonate / chloroform

10.2: 20 °C / Reflux

With hydrogenchloride; dmap; dipotassium hydrogenphosphate; hydrogen; diethylzinc; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; palladium 10% on activated carbon; palladium(II) hydroxide; In 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

4-ethynyl-piperidine-1-carboxylic acid tert-butyl ester

tert-butyl 4-[(4R)-5-(benzyloxy)-4-hydroxypent-1-yn-1-yl]piperidine-1-carboxylate

C₂₅H₃₀FNO₅S

benzyl 4-[(1R,2S)-2-(2-hydroxyethyl)cyclopropyl]piperidine-1-carboxylate

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