4'-[(2S,3S,4S)-4-benzyl-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]-2'-chlorobenzonitrile

Base Information

Chemical Name:4'-[(2S,3S,4S)-4-benzyl-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]-2'-chlorobenzonitrile
CAS No.:1114545-78-6
Molecular Formula:C₁₉H₁₇ClN₂O₂
Molecular Weight:340.809
Hs Code.:

Synonyms:4'-[(2S,3S,4S)-4-benzyl-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]-2'-chlorobenzonitrile

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Chemical Property of 4'-[(2S,3S,4S)-4-benzyl-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]-2'-chlorobenzonitrile

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Technology Process of 4'-[(2S,3S,4S)-4-benzyl-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]-2'-chlorobenzonitrile

There total 2 articles about 4'-[(2S,3S,4S)-4-benzyl-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]-2'-chlorobenzonitrile 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: 30.0%

: 1114545-61-7
2'-chloro-4'-[(2S,3S)-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]benzonitrile

: 100-39-0
benzyl bromide

: 1114545-78-6
4'-[(2S,3S,4S)-4-benzyl-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]-2'-chlorobenzonitrile

Guidance literature:: With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

2'-chloro-4'-[(2S,3S)-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]benzonitrile; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

benzyl bromide; In tetrahydrofuran; hexane; at -78 - -30 ℃; for 1h;

Reference yield:

: 151004-19-2
(4S,5S)-5-methyl-4-hydroxy-2-oxopyrrolidine

: 1114545-78-6
4'-[(2S,3S,4S)-4-benzyl-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]-2'-chlorobenzonitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1H-imidazole / 18 h / 0 - 20 °C

2.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 12 h / 80 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 °C

3.2: 1 h / -78 - -30 °C

With 1H-imidazole; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; caesium carbonate; diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; hexane; 2.1: |Buchwald-Hartwig Coupling;
DOI:10.1016/j.bmc.2017.04.018