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

Base Information

Chemical Name:2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-yl)acetic acid
CAS No.:1234387-34-8
Molecular Formula:C₂₀H₃₀BrNO₄Si
Molecular Weight:456.452
Hs Code.:

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

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Chemical Property of 2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-yl)acetic acid

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Technology Process of 2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-yl)acetic acid

There total 10 articles about 2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tertbutyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-yl)acetic 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: 86.0%

: 1234387-32-6
2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-yl)acetaldehyde

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

Guidance literature:: With potassium permanganate; In tert-butyl alcohol; at 20 ℃; for 5h; Alkaline conditions;
DOI:10.1002/cjoc.201300363

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 8 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

With hydrogenchloride; triethylsilane; potassium permanganate; thionyl chloride; sodium; titanium tetrachloride; sodium hydride; ozone; 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

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

Guidance literature:: Multi-step reaction with 7 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

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