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

Base Information

• Chemical Name: 1-((3S)-4-(4-chlorobenzyl)-7-fluoro-3-(hydroxymethyl)-1,2,3,4-tetrahydrocyclo-penta[b]indol-5-yl)ethanone
• CAS No.: 1009099-50-6
• Molecular Formula: C₂₁H₁₉ClFNO₂
• Molecular Weight: 371.839
• Mol file: 1009099-50-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about 1-((3S)-4-(4-chlorobenzyl)-7-fluoro-3-(hydroxymethyl)-1,2,3,4-tetrahydrocyclo-penta[b]indol-5-yl)ethanone 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: 100.0%

acetic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester (1026405-15-1) → 1-((3S)-4-(4-chlorobenzyl)-7-fluoro-3-(hydroxymethyl)-1,2,3,4-tetrahydrocyclo-penta[b]indol-5-yl)ethanone (1009099-50-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; for 0.25h; Heating;

DOI:10.1002/jlcr.1146

Reference yield:

[(3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid (393509-05-2) → 1-((3S)-4-(4-chlorobenzyl)-7-fluoro-3-(hydroxymethyl)-1,2,3,4-tetrahydrocyclo-penta[b]indol-5-yl)ethanone (1009099-50-6)

Guidance literature:

Multi-step reaction with 8 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

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) → 1-((3S)-4-(4-chlorobenzyl)-7-fluoro-3-(hydroxymethyl)-1,2,3,4-tetrahydrocyclo-penta[b]indol-5-yl)ethanone (1009099-50-6)

Guidance literature:

Multi-step reaction with 7 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

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

upstream raw materials:

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

[(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

((3S)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)methanol

Downstream raw materials:

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