2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxo-pyrrolidin-3-yl)-N-(3-chloro-2-methylphenyl)acetamide

Base Information

Chemical Name:2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxo-pyrrolidin-3-yl)-N-(3-chloro-2-methylphenyl)acetamide
CAS No.:1234387-36-0
Molecular Formula:C₂₇H₃₆BrClN₂O₃Si
Molecular Weight:580.037
Hs Code.:

Synonyms:2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxo-pyrrolidin-3-yl)-N-(3-chloro-2-methylphenyl)acetamide

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Chemical Property of 2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxo-pyrrolidin-3-yl)-N-(3-chloro-2-methylphenyl)acetamide

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Technology Process of 2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxo-pyrrolidin-3-yl)-N-(3-chloro-2-methylphenyl)acetamide

There total 11 articles about 2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxo-pyrrolidin-3-yl)-N-(3-chloro-2-methylphenyl)acetamide 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: 28.0%

: 1234387-34-8
2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-yl)acetic acid

: 87-60-5
3-chloro-2-methylbenzenamine

: 1234387-36-0
2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxo-pyrrolidin-3-yl)-N-(3-chloro-2-methylphenyl)acetamide

Guidance literature:: 2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-yl)acetic acid; With dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 0.25h;

3-chloro-2-methylbenzenamine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1002/cjoc.201300363

Reference yield:

: 405522-29-4
(3S,7aS)-7a-(4-bromophenyl)-3-phenyltetrahydropyrrolo[2,1-b]oxazol-5(6H)-one

: 1234387-36-0
2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxo-pyrrolidin-3-yl)-N-(3-chloro-2-methylphenyl)acetamide

Guidance literature:: Multi-step reaction with 9 steps

1.1: titanium tetrachloride; triethylsilane / dichloromethane / 16 h / -78 °C

2.1: thionyl chloride / tetrahydrofuran / 2 h / 0 - 20 °C

3.1: sodium / ethanol / 4 h / 45 °C

4.1: hydrogenchloride / tetrahydrofuran; water / 3 h / Reflux

5.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Reflux

6.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

6.2: -78 - 20 °C / Inert atmosphere

7.1: ozone / dichloromethane / -78 °C

7.2: -78 - 20 °C / Inert atmosphere

8.1: potassium permanganate / tert-butyl alcohol / 5 h / 20 °C / Alkaline conditions

9.1: dicyclohexyl-carbodiimide / dichloromethane / 0.25 h / 0 °C

9.2: 0.5 h / 0 °C

With hydrogenchloride; triethylsilane; potassium permanganate; thionyl chloride; sodium; titanium tetrachloride; sodium hydride; ozone; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/cjoc.201300363

Reference yield:

: 405522-31-8
(R)-5-(4-bromophenyl)-1-((S)-2-hydroxy-1-phenylethyl)pyrrolidin-2-one

: 1234387-36-0
2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxo-pyrrolidin-3-yl)-N-(3-chloro-2-methylphenyl)acetamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: thionyl chloride / tetrahydrofuran / 2 h / 0 - 20 °C

2.1: sodium / ethanol / 4 h / 45 °C

3.1: hydrogenchloride / tetrahydrofuran; water / 3 h / Reflux

4.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Reflux

5.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

5.2: -78 - 20 °C / Inert atmosphere

6.1: ozone / dichloromethane / -78 °C

6.2: -78 - 20 °C / Inert atmosphere

7.1: potassium permanganate / tert-butyl alcohol / 5 h / 20 °C / Alkaline conditions

8.1: dicyclohexyl-carbodiimide / dichloromethane / 0.25 h / 0 °C

8.2: 0.5 h / 0 °C

With hydrogenchloride; potassium permanganate; thionyl chloride; sodium; sodium hydride; ozone; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/cjoc.201300363