3-{1-[(1R,3S)-3-{[3,5-bis(trifluoromethyl)benzyl]carbamoyl}-3-isopropylcyclopentyl]piperidin-4-yl}benzoic acid

Base Information

• Chemical Name: 3-{1-[(1R,3S)-3-{[3,5-bis(trifluoromethyl)benzyl]carbamoyl}-3-isopropylcyclopentyl]piperidin-4-yl}benzoic acid
• CAS No.: 1204403-89-3
• Molecular Formula: C₃₀H₃₄F₆N₂O₃
• Molecular Weight: 584.602
• Mol file: 1204403-89-3.mol

Synonyms:3-{1-[(1R,3S)-3-{[3,5-bis(trifluoromethyl)benzyl]carbamoyl}-3-isopropylcyclopentyl]piperidin-4-yl}benzoic acid

Chemical Property of 3-{1-[(1R,3S)-3-{[3,5-bis(trifluoromethyl)benzyl]carbamoyl}-3-isopropylcyclopentyl]piperidin-4-yl}benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{1-[(1R,3S)-3-{[3,5-bis(trifluoromethyl)benzyl]carbamoyl}-3-isopropylcyclopentyl]piperidin-4-yl}benzoic acid

There total 7 articles about 3-{1-[(1R,3S)-3-{[3,5-bis(trifluoromethyl)benzyl]carbamoyl}-3-isopropylcyclopentyl]piperidin-4-yl}benzoic acid 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: 53.0%

methyl 3-(1-((1R,3S)-3-((3,5-bis(trifluoromethyl)benzyl)carbamoyl)-3-isopropylcyclopentyl)piperidin-4-yl)benzoate trifluoroacetate → 3-{1-[(1R,3S)-3-{[3,5-bis(trifluoromethyl)benzyl]carbamoyl}-3-isopropylcyclopentyl]piperidin-4-yl}benzoic acid (1204403-89-3)

Guidance literature:

With lithium hydroxide; In ethanol; water; at 50 ℃; for 1.5h;

DOI:10.1002/cmdc.201500058

Reference yield:

1-Methyl-4-piperidone (1445-73-4) → 3-{1-[(1R,3S)-3-{[3,5-bis(trifluoromethyl)benzyl]carbamoyl}-3-isopropylcyclopentyl]piperidin-4-yl}benzoic acid (1204403-89-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetone / 5 h / 60 °C / Inert atmosphere

2.1: potassium carbonate / ethanol; water / 5 h / Reflux

3.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran / 1 h / -78 - -20 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: lithium chloride; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,2-dimethoxyethane / 3.5 h / 90 °C / Inert atmosphere; Microwave irradiation

5.1: palladium diacetate; hydrogen; palladium on activated carbon / methanol

6.1: lithium hydroxide / ethanol; water / 1.5 h / 50 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium on activated carbon; hydrogen; palladium diacetate; sodium carbonate; potassium carbonate; lithium chloride; lithium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; n-heptane; water; acetone; 4.1: |Suzuki Coupling;

DOI:10.1002/cmdc.201500058

Reference yield:

methyl 3-(1-((1R,3S)-3-((3,5-bis(trifluoromethyl)benzyl)carbamoyl)-3-isopropylcyclopentyl)-1,2,3,6-tetrahydropyridin-4-yl)benzoate → 3-{1-[(1R,3S)-3-{[3,5-bis(trifluoromethyl)benzyl]carbamoyl}-3-isopropylcyclopentyl]piperidin-4-yl}benzoic acid (1204403-89-3)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; hydrogen; palladium on activated carbon / methanol

2: lithium hydroxide / ethanol; water / 1.5 h / 50 °C

With palladium on activated carbon; hydrogen; palladium diacetate; lithium hydroxide; In methanol; ethanol; water;

DOI:10.1002/cmdc.201500058

upstream raw materials:

1-Methyl-4-piperidone

1-methyl-1-ethyl-4-oxopiperidinium iodide

(1S,3R)-3-amino-N-[3,5-bis(trifluoromethyl)benzyl]-1-isopropylcyclopentane-1-carboxamide