(S)-3-(1-benzyl-4-ethyl-1H-indol-7-yl)butanoic acid

Base Information

Chemical Name:(S)-3-(1-benzyl-4-ethyl-1H-indol-7-yl)butanoic acid
CAS No.:1443436-98-3
Molecular Formula:C₂₁H₂₃NO₂
Molecular Weight:321.419
Hs Code.:

Synonyms:(S)-3-(1-benzyl-4-ethyl-1H-indol-7-yl)butanoic acid

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Chemical Property of (S)-3-(1-benzyl-4-ethyl-1H-indol-7-yl)butanoic acid

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Technology Process of (S)-3-(1-benzyl-4-ethyl-1H-indol-7-yl)butanoic acid

There total 7 articles about (S)-3-(1-benzyl-4-ethyl-1H-indol-7-yl)butanoic 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: 32.0%

: 161988-76-7
3-(7-(1-benzyl-4-ethyl)-indolyl)-butanoic acid methylester

: methyl (3S)-3-(1-benzyl-4-ethyl-1H-indol-7-yl)butanoate

: 1443436-98-3
(S)-3-(1-benzyl-4-ethyl-1H-indol-7-yl)butanoic acid

: 1443437-02-2
methyl (3R)-3-(1-benzyl-4-ethyl-1H-indol-7-yl)butanoate

Guidance literature:: With Amano lipase PS-IM (immobilized on diatomaceous earth); In di-isopropyl ether; water; at 40 ℃; for 65h; Reagent/catalyst; Solvent; enantioselective reaction; Resolution of racemate; Enzymatic reaction;
DOI:10.1002/chem.201202413

Reference yield:

: 161988-90-5
7-bromo-4-ethyl-1H-indole

: 1443436-98-3
(S)-3-(1-benzyl-4-ethyl-1H-indol-7-yl)butanoic acid

: 1443437-02-2
methyl (3R)-3-(1-benzyl-4-ethyl-1H-indol-7-yl)butanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium hydroxide / dimethyl sulfoxide / 0.5 h

1.2: 12 h / 20 °C

2.1: palladium dichloride; triethylamine; tris-(o-tolyl)phosphine / acetonitrile / 15 h / 110 °C / Schlenk technique; Inert atmosphere

3.1: magnesium; methanol / 13 h / Reflux

4.1: Amano lipase PS-IM (immobilized on diatomaceous earth) / water; di-isopropyl ether / 65 h / 40 °C / Resolution of racemate; Enzymatic reaction

With methanol; Amano lipase PS-IM (immobilized on diatomaceous earth); magnesium; triethylamine; tris-(o-tolyl)phosphine; potassium hydroxide; palladium dichloride; In di-isopropyl ether; water; dimethyl sulfoxide; acetonitrile;
DOI:10.1002/chem.201202413

Reference yield:

: 18640-58-9
3-nitro-4-bromoacetophenone

: 1443436-98-3
(S)-3-(1-benzyl-4-ethyl-1H-indol-7-yl)butanoic acid

: 1443437-02-2
methyl (3R)-3-(1-benzyl-4-ethyl-1H-indol-7-yl)butanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium tetrahydroborate / methanol / 0.5 h / 0 - 20 °C

2.1: 1H-imidazole; triphenylphosphine; iodine / dichloromethane / 3 h / 0 °C

2.2: 0.5 h / 0 - 20 °C

3.1: tetrahydrofuran / 0.75 h / -45 °C / Schlenk technique; Inert atmosphere

4.1: potassium hydroxide / dimethyl sulfoxide / 0.5 h

4.2: 12 h / 20 °C

5.1: palladium dichloride; triethylamine; tris-(o-tolyl)phosphine / acetonitrile / 15 h / 110 °C / Schlenk technique; Inert atmosphere

6.1: magnesium; methanol / 13 h / Reflux

7.1: Amano lipase PS-IM (immobilized on diatomaceous earth) / water; di-isopropyl ether / 65 h / 40 °C / Resolution of racemate; Enzymatic reaction

With 1H-imidazole; methanol; sodium tetrahydroborate; Amano lipase PS-IM (immobilized on diatomaceous earth); iodine; magnesium; triethylamine; triphenylphosphine; tris-(o-tolyl)phosphine; potassium hydroxide; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; di-isopropyl ether; water; dimethyl sulfoxide; acetonitrile; 3.1: |Bartoli Indole Synthesis;
DOI:10.1002/chem.201202413