2'-chloro-4'-[(2S,3S)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]benzonitrile

Base Information

Chemical Name:2'-chloro-4'-[(2S,3S)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]benzonitrile
CAS No.:1114545-97-9
Molecular Formula:C₁₃H₁₃ClN₂O₂
Molecular Weight:264.711
Hs Code.:

Synonyms:2'-chloro-4'-[(2S,3S)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]benzonitrile

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Chemical Property of 2'-chloro-4'-[(2S,3S)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]benzonitrile

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Technology Process of 2'-chloro-4'-[(2S,3S)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]benzonitrile

There total 6 articles about 2'-chloro-4'-[(2S,3S)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]benzonitrile 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: 24.0%

: 1114547-19-1
4-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-ethyl-5-oxopyrrolidin-1-yl]-2-chlorobenzonitrile

: 1114545-97-9
2'-chloro-4'-[(2S,3S)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]benzonitrile

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; methanol; water; at 20 ℃; for 72h;

Reference yield: 18.0%

: 1114547-15-7
(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-ethylpyrrolidin-5-one

: 1114545-97-9
2'-chloro-4'-[(2S,3S)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]benzonitrile

Guidance literature:: (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-ethylpyrrolidin-5-one; 4-halo-2-chlorobenzonitrile; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 80 ℃; for 12h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; 1,4-dioxane; ethanol; water; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.bmc.2017.04.018

Reference yield:

: 1114547-11-3
ethyl (4S)-4-[(benzyloxy)carbonyl]amino-3-hydroxyhexanoate

: 1114545-97-9
2'-chloro-4'-[(2S,3S)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]benzonitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,6-dimethylpyridine / tetrahydrofuran / 1 h / 0 - 20 °C

2.1: palladium 10% on activated carbon; hydrogen / methanol / 3.5 h / 20 °C

2.2: 1 h / 20 °C

3.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 12 h / 80 °C / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium 10% on activated carbon; hydrogen; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; methanol; 3.1: |Buchwald-Hartwig Coupling;
DOI:10.1016/j.bmc.2017.04.018