methanesulfonic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester

Base Information

• Chemical Name: methanesulfonic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester
• CAS No.: 1027400-35-6
• Molecular Formula: C₂₂H₂₁ClFNO₄S
• Molecular Weight: 449.93
• Mol file: 1027400-35-6.mol

Synonyms:

Chemical Property of methanesulfonic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methanesulfonic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester

There total 9 articles about methanesulfonic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester 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:

[(3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid (393509-05-2) → methanesulfonic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester (1027400-35-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 100 percent / diethyl ether

2.1: KHMDS / tetrahydrofuran / 0.25 h / -78 °C

2.2: oxaziridine / tetrahydrofuran / 1 h

3.1: DIBAL-H / tetrahydrofuran; hexane / 1 h / -40 °C

4.1: sodium periodate / tetrahydrofuran; H₂O / 20 °C

5.1: DIBAL-H / tetrahydrofuran; toluene; hexane / -78 - -40 °C

6.1: 100 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 °C

7.1: triphenyl arsine / Pd₂(dba)3 / dimethylformamide / 18 h / 90 °C

7.2: 67 percent / aq. HCl / dimethylformamide / 35 °C

8.1: 100 percent / sodium hydroxide / tetrahydrofuran; methanol / 0.25 h / Heating

9.1: triethylamine / CH₂Cl₂ / -30 - 20 °C

With dmap; sodium hydroxide; sodium periodate; triphenyl-arsane; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 7.1: Stille coupling;

DOI:10.1002/jlcr.1146

Reference yield:

[5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester (571170-89-3) → methanesulfonic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester (1027400-35-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: KHMDS / tetrahydrofuran / 0.25 h / -78 °C

1.2: oxaziridine / tetrahydrofuran / 1 h

2.1: DIBAL-H / tetrahydrofuran; hexane / 1 h / -40 °C

3.1: sodium periodate / tetrahydrofuran; H₂O / 20 °C

4.1: DIBAL-H / tetrahydrofuran; toluene; hexane / -78 - -40 °C

5.1: 100 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 °C

6.1: triphenyl arsine / Pd₂(dba)3 / dimethylformamide / 18 h / 90 °C

6.2: 67 percent / aq. HCl / dimethylformamide / 35 °C

7.1: 100 percent / sodium hydroxide / tetrahydrofuran; methanol / 0.25 h / Heating

8.1: triethylamine / CH₂Cl₂ / -30 - 20 °C

With dmap; sodium hydroxide; sodium periodate; triphenyl-arsane; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 6.1: Stille coupling;

DOI:10.1002/jlcr.1146

Reference yield:

5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indole-3-carbaldehyde → methanesulfonic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester (1027400-35-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: DIBAL-H / tetrahydrofuran; toluene; hexane / -78 - -40 °C

2.1: 100 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 °C

3.1: triphenyl arsine / Pd₂(dba)3 / dimethylformamide / 18 h / 90 °C

3.2: 67 percent / aq. HCl / dimethylformamide / 35 °C

4.1: 100 percent / sodium hydroxide / tetrahydrofuran; methanol / 0.25 h / Heating

5.1: triethylamine / CH₂Cl₂ / -30 - 20 °C

With dmap; sodium hydroxide; triphenyl-arsane; diisobutylaluminium hydride; triethylamine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: Stille coupling;

DOI:10.1002/jlcr.1146

upstream raw materials:

1-((3S)-4-(4-chlorobenzyl)-7-fluoro-3-(hydroxymethyl)-1,2,3,4-tetrahydrocyclo-penta[b]indol-5-yl)ethanone

methanesulfonyl chloride

[(3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid

[5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester