(R)-2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid

Base Information

• Chemical Name: (R)-2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid
• CAS No.: 1215119-45-1
• Molecular Formula: C₂₅H₂₆F₃NO₄
• Molecular Weight: 461.481

Synonyms:(R)-2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid

Chemical Property of (R)-2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of (R)-2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid

There total 13 articles about (R)-2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic 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:

2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid (1215118-50-5) → (S)-2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid (1215119-44-0) + (R)-2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid (1215119-45-1)

Guidance literature:

With trifluoroacetic acid; In hexanes; ipa; Resolution of racemate;

Reference yield:

5-benzyloxy-1H-indole-2-carboxylic acid ethyl ester (37033-95-7) → (S)-2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid (1215119-44-0) + (R)-2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid (1215119-45-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium hydride / toluene; mineral oil / 0.83 h

1.2: 20 - 70 °C

1.3: 24 h / Reflux

2.1: tetrahydrofuran / 24 h / Reflux

3.1: hydrogen / palladium 10% on activated carbon / water; tetrahydrofuran / 24 h / 11636.1 Torr

4.1: hydrogen; acetic acid / 20 % Pd(OH)2/C / ethanol; tetrahydrofuran / 50 °C / 10343.2 - 25858.1 Torr

5.1: palladium on carbon / toluene / 48 h / 80 °C

6.1: caesium carbonate / ISOPROPYLAMIDE / 16 h / 80 °C

7.1: N-iodo-succinimide / dichloromethane / 0.08 h / 0 °C

8.1: bis(tri-t-butylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / Inert atmosphere

9.1: water; lithium hydroxide / dioxanes / 16 h / 75 °C

10.1: trifluoroacetic acid / ipa; hexanes / Resolution of racemate

With N-iodo-succinimide; water; hydrogen; sodium hydride; caesium carbonate; acetic acid; trifluoroacetic acid; lithium hydroxide; bis(tri-t-butylphosphine)palladium⁽⁰⁾; 20 % Pd(OH)2/C; palladium on carbon; palladium 10% on activated carbon; In tetrahydrofuran; hexanes; ipa; dioxanes; ethanol; dichloromethane; ISOPROPYLAMIDE; water; toluene; mineral oil;

Reference yield:

ethyl 5-bromoindolecarboxylate (16732-70-0) → (S)-2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid (1215119-44-0) + (R)-2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid (1215119-45-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium hydride / toluene; mineral oil / 110 °C

1.2: 48 h / 110 °C

1.3: 16 h / Reflux

2.1: tetrahydrofuran / 16 h / 65 °C

3.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1.5 h / 90 °C / Inert atmosphere

4.1: sodium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 0.42 h / 23 °C

5.1: hydrogen / palladium 10% on activated carbon / ethyl acetate; water / 3 h / 4913.04 Torr

6.1: caesium carbonate / ISOPROPYLAMIDE / 16 h / 80 °C

7.1: N-iodo-succinimide / dichloromethane / 0.08 h / 0 °C

8.1: bis(tri-t-butylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / Inert atmosphere

9.1: water; lithium hydroxide / dioxanes / 16 h / 75 °C

10.1: trifluoroacetic acid / ipa; hexanes / Resolution of racemate

With N-iodo-succinimide; water; hydrogen; dihydrogen peroxide; potassium acetate; sodium hydride; caesium carbonate; trifluoroacetic acid; sodium hydroxide; lithium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(tri-t-butylphosphine)palladium⁽⁰⁾; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; hexanes; ipa; dioxanes; dichloromethane; ISOPROPYLAMIDE; water; ethyl acetate; toluene; mineral oil;

upstream raw materials:

5-benzyloxy-1H-indole-2-carboxylic acid ethyl ester

ethyl 5-bromoindolecarboxylate

tert-butyl 2-(7-(benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

tert-butyl 2-(7-hydroxy-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

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