tert-butyl (2R,5S)-2-(4-{[(6-bromopyridin-2-yl)methyl](methyl)carbamoyl}benzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-pyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (2R,5S)-2-(4-{[(6-bromopyridin-2-yl)methyl](methyl)carbamoyl}benzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-pyrrolidine-1-carboxylate
• CAS No.: 1269615-54-4
• Molecular Formula: C₃₇H₅₀BrN₃O₄Si
• Molecular Weight: 708.811
• Mol file: 1269615-54-4.mol

Synonyms:tert-butyl (2R,5S)-2-(4-{[(6-bromopyridin-2-yl)methyl](methyl)carbamoyl}benzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-pyrrolidine-1-carboxylate

Chemical Property of tert-butyl (2R,5S)-2-(4-{[(6-bromopyridin-2-yl)methyl](methyl)carbamoyl}benzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2R,5S)-2-(4-{[(6-bromopyridin-2-yl)methyl](methyl)carbamoyl}benzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-pyrrolidine-1-carboxylate

There total 19 articles about tert-butyl (2R,5S)-2-(4-{[(6-bromopyridin-2-yl)methyl](methyl)carbamoyl}benzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-pyrrolidine-1-carboxylate 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: 27.0%

1-(6-bromopyridin-2-yl)-N-methylmethanamine (675109-37-2) + 4-(((2S,5R)-1-(tert-butoxycarbonyl)-5-((R)-((tert-butyldimethylsilyl)oxy)(phenyl)methyl)pyrrolidin-2-yl)methyl)benzoic acid (1269429-21-1) → tert-butyl (2R,5S)-2-(4-{[(6-bromopyridin-2-yl)methyl](methyl)carbamoyl}benzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-pyrrolidine-1-carboxylate (1269615-54-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

Reference yield:

1,4-bromoiodobenzene (589-87-7) → tert-butyl (2R,5S)-2-(4-{[(6-bromopyridin-2-yl)methyl](methyl)carbamoyl}benzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-pyrrolidine-1-carboxylate (1269615-54-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triethylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; copper(l) iodide / N,N-dimethyl-formamide / 6 h / 20 °C

2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

3.1: platinum(II) chloride / toluene / 6 h / 80 °C / Inert atmosphere

4.1: sodium tris(acetoxy)borohydride / dichloromethane / 0 - 20 °C

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

6.1: triethylamine / palladium diacetate / 120 °C

7.1: water; lithium hydroxide / methanol / 20 °C

7.2: pH 4.5

8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 12 h / 20 °C

With water; sodium tris(acetoxy)borohydride; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; lithium hydroxide; copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium diacetate; platinum(II) chloride; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

4-methoxybenzyl {(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pent-4-yn-1-yl}carbamate (1190391-64-0) → tert-butyl (2R,5S)-2-(4-{[(6-bromopyridin-2-yl)methyl](methyl)carbamoyl}benzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-pyrrolidine-1-carboxylate (1269615-54-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triethylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; copper(l) iodide / N,N-dimethyl-formamide / 6 h / 20 °C

2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

3.1: platinum(II) chloride / toluene / 6 h / 80 °C / Inert atmosphere

4.1: sodium tris(acetoxy)borohydride / dichloromethane / 0 - 20 °C

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

6.1: triethylamine / palladium diacetate / 120 °C

7.1: water; lithium hydroxide / methanol / 20 °C

7.2: pH 4.5

8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 12 h / 20 °C

With water; sodium tris(acetoxy)borohydride; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; lithium hydroxide; copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium diacetate; platinum(II) chloride; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

1,4-bromoiodobenzene

1-(6-bromopyridin-2-yl)-N-methylmethanamine

4-(((2S,5R)-1-(tert-butoxycarbonyl)-5-((R)-((tert-butyldimethylsilyl)oxy)(phenyl)methyl)pyrrolidin-2-yl)methyl)benzoic acid

4-methoxybenzyl {(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pent-4-yn-1-yl}carbamate

Downstream raw materials:

tert-butyl (2S,5R)-2-(4-{[(6-aminopyridin-2-yl)methyl](methyl)carbamoyl}benzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-pyrrolidine-1-carboxylate