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

Base Information

Chemical Name:2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-yl)acetaldehyde
CAS No.:1234387-32-6
Molecular Formula:C₂₀H₃₀BrNO₃Si
Molecular Weight:440.453
Hs Code.:

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

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Chemical Property of 2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-yl)acetaldehyde

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Technology Process of 2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-yl)acetaldehyde

There total 9 articles about 2-((3R,5R)-5-(4-bromophenyl)-1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-yl)acetaldehyde 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: 76.0%

: 1234387-31-5
(3S,5R)-3-allyl-5-(4-bromophenyl)-1-(2-(tert-butyldimethylsilyloxy)ethyl)pyrrolidin-2-one

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

Guidance literature:: (3S,5R)-3-allyl-5-(4-bromophenyl)-1-(2-(tert-butyldimethylsilyloxy)ethyl)pyrrolidin-2-one; With ozone; In dichloromethane; at -78 ℃;

With triphenylphosphine; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;
DOI:10.1002/cjoc.201300363

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

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