(2S,4S)-1-(3-(allyloxy)-2-iodobenzyl)-4-(tert-butyldimethylsilyloxy)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide

Base Information

• Chemical Name: (2S,4S)-1-(3-(allyloxy)-2-iodobenzyl)-4-(tert-butyldimethylsilyloxy)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide
• CAS No.: 1352212-87-3
• Molecular Formula: C₂₈H₃₉IN₂O₃Si
• Molecular Weight: 606.619

Synonyms:(2S,4S)-1-(3-(allyloxy)-2-iodobenzyl)-4-(tert-butyldimethylsilyloxy)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide

Chemical Property of (2S,4S)-1-(3-(allyloxy)-2-iodobenzyl)-4-(tert-butyldimethylsilyloxy)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide

Chemical Property:

Purity/Quality:

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Technology Process of (2S,4S)-1-(3-(allyloxy)-2-iodobenzyl)-4-(tert-butyldimethylsilyloxy)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide

There total 15 articles about (2S,4S)-1-(3-(allyloxy)-2-iodobenzyl)-4-(tert-butyldimethylsilyloxy)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide 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: 87.0%

3-(allyloxy)-2-iodobenzaldehyde (1352212-84-0) + (2S,4S)-4-(tert-butyldimethylsilyloxy)-N-methyl-N-phenylpyrrolidine-2-carboxamide (1352212-83-9) → (2S,4S)-1-(3-(allyloxy)-2-iodobenzyl)-4-(tert-butyldimethylsilyloxy)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide (1352212-87-3)

Guidance literature:

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2011.10.010

Reference yield:

(2S,4S)-1-(tert-butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid (401564-17-8) → (2S,4S)-1-(3-(allyloxy)-2-iodobenzyl)-4-(tert-butyldimethylsilyloxy)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide (1352212-87-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

2.1: tetrahydrofuran / 20 h / 0 °C / Inert atmosphere; Reflux

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

3.2: 0.25 h / 0 °C / Inert atmosphere

4.1: zinc dibromide / dichloromethane / 0 - 20 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere

With sodium tris(acetoxy)borohydride; sodium hydride; triethylamine; zinc dibromide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.bmc.2011.10.010

Reference yield:

C18H33NO7Si → (2S,4S)-1-(3-(allyloxy)-2-iodobenzyl)-4-(tert-butyldimethylsilyloxy)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide (1352212-87-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 20 h / 0 °C / Inert atmosphere; Reflux

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

2.2: 0.25 h / 0 °C / Inert atmosphere

3.1: zinc dibromide / dichloromethane / 0 - 20 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere

With sodium tris(acetoxy)borohydride; sodium hydride; zinc dibromide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.bmc.2011.10.010

upstream raw materials:

(2S,4S)-1-(tert-butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid

3-(allyloxy)-2-iodobenzaldehyde

(2S,4S)-4-(tert-butyldimethylsilyloxy)-N-methyl-N-phenylpyrrolidine-2-carboxamide

(2S,4S)-tert-butyl 4-(tert-butyldimethylsilyloxy)-2-(N-methyl-N-phenylcarbamoyl)-pyrrolidine-1-carboxylate

Downstream raw materials:

(2S,10S,10aS)-9-allyloxy-10-benzoyloxy-2-hydroxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinoline

(2S,10S,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-(allyloxy)phenyl)-propanoate

(2S,10S,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-(but-3-enyloxy)phenyl)-propanoate

(2S,10S,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-allylphenyl)-propanoate

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