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

Base Information

• Chemical Name: (3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-ol
• CAS No.: 869194-37-6
• Molecular Formula: C₁₈H₁₄BrClFNO
• Molecular Weight: 394.671

Synonyms:(3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-ol

Chemical Property of (3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-ol

Chemical Property:

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Technology Process of (3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-ol

There total 3 articles about (3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-ol 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: 98.0%

5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,4-dihydrocyclopenta[b]indol-3(2H)-one (869194-32-1) → (3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-ol (869194-37-6)

Guidance literature:

With dimethylsulfide borane complex; (S)-oxazaborolidine; In dichloromethane; at -20 ℃; for 3.5h;

DOI:10.1021/jo051146p

Reference yield:

5-bromo-7-fluoro-1,4-dihydrocyclopenta[b]indol-3(2H)-one (869194-30-9) → (3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-ol (869194-37-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / tetrabutylammonium bromide; aq. NaOH / tetrahydrofuran; various solvent(s) / 22 h / 50 °C

2: 98 percent / (S)-oxazaborolidine; BH₃*DMS / CH₂Cl₂ / 3.5 h / -20 °C

With sodium hydroxide; dimethylsulfide borane complex; (S)-oxazaborolidine; tetrabutylammomium bromide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo051146p

Reference yield:

1-Chloro-4-(chloromethyl)benzene (104-83-6) → (3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-ol (869194-37-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / tetrabutylammonium bromide; aq. NaOH / tetrahydrofuran; various solvent(s) / 22 h / 50 °C

2: 98 percent / (S)-oxazaborolidine; BH₃*DMS / CH₂Cl₂ / 3.5 h / -20 °C

With sodium hydroxide; dimethylsulfide borane complex; (S)-oxazaborolidine; tetrabutylammomium bromide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo051146p

upstream raw materials:

5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,4-dihydrocyclopenta[b]indol-3(2H)-one

5-bromo-7-fluoro-1,4-dihydrocyclopenta[b]indol-3(2H)-one

1-Chloro-4-(chloromethyl)benzene

Downstream raw materials:

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

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

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