(2S,5R)-tert-butyl 2-(4-aminobenzyl)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (2S,5R)-tert-butyl 2-(4-aminobenzyl)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate
• CAS No.: 1190615-16-7
• Molecular Formula: C₂₂H₂₉N₃O₃
• Molecular Weight: 383.491
• Mol file: 1190615-16-7.mol

Synonyms:(2S,5R)-tert-butyl 2-(4-aminobenzyl)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate

Chemical Property of (2S,5R)-tert-butyl 2-(4-aminobenzyl)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-tert-butyl 2-(4-aminobenzyl)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate

There total 13 articles about (2S,5R)-tert-butyl 2-(4-aminobenzyl)-5-((R)-hydroxy(pyridin-3-yl)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: 87.0%

(2S,5R)-tert-butyl-2-(4-aminobenzyl)-5-((R)-((tert-butyldimethylsilyl) oxy)(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate (1190615-04-3) → (2S,5R)-tert-butyl 2-(4-aminobenzyl)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate (1190615-16-7)

Guidance literature:

(2S,5R)-tert-butyl-2-(4-aminobenzyl)-5-((R)-((tert-butyldimethylsilyl) oxy)(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate; With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 7h;

With water; In tetrahydrofuran;

Reference yield:

C25H29ClN2O4Si → (2S,5R)-tert-butyl 2-(4-aminobenzyl)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate (1190615-16-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: trifluoroacetic acid / methanol / 1.5 h / Inert atmosphere

2.1: 2,6-dimethylpyridine; t-butyldimethylsiyl triflate / dichloromethane / 0 - 25 °C / Inert atmosphere

3.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 0 - 25 °C / Inert atmosphere

4.1: triethylamine; diphenyl phosphoryl azide / toluene / 5 h / 25 °C / Inert atmosphere

4.2: 13 h / 80 - 110 °C / Inert atmosphere

5.1: triethylamine; C₃₄H₂₉Cl₂FeP₂Pd⁽¹⁺⁾; copper(l) iodide / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere

6.1: pyrrolidine / N,N-dimethyl-formamide / 2 h / Inert atmosphere; Heating

6.2: 3 h / Inert atmosphere

7.1: trifluoroacetic acid / dichloromethane / 1.5 h / Inert atmosphere

8.1: sodium tris(acetoxy)borohydride / dichloromethane / 12 h / 0 - 25 °C / Inert atmosphere

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 °C / Inert atmosphere

10.1: hydrogen; palladium 10% on activated carbon; potassium acetate / methanol / 12 h / 2585.81 Torr

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Heating

With pyrrolidine; 2,6-dimethylpyridine; copper(l) iodide; diphenyl phosphoryl azide; palladium 10% on activated carbon; t-butyldimethylsiyl triflate; C₃₄H₂₉Cl₂FeP₂Pd⁽¹⁺⁾; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; potassium acetate; sodium tris(acetoxy)borohydride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 4.1: |Curtius Rearrangement / 4.2: |Curtius Rearrangement / 5.1: |Sonogashira Cross-Coupling;

DOI:10.1021/jm4017224

Reference yield:

4-methoxybenzyl ((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(6-chloropyridin-3-yl)-6-(4-nitrophenyl)hex-5-yn-2-yl)carbamate (1190615-01-0) → (2S,5R)-tert-butyl 2-(4-aminobenzyl)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate (1190615-16-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyrrolidine / N,N-dimethyl-formamide / 2 h / Inert atmosphere; Heating

1.2: 3 h / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 1.5 h / Inert atmosphere

3.1: sodium tris(acetoxy)borohydride / dichloromethane / 12 h / 0 - 25 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 °C / Inert atmosphere

5.1: hydrogen; palladium 10% on activated carbon; potassium acetate / methanol / 12 h / 2585.81 Torr

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Heating

With pyrrolidine; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; potassium acetate; sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm4017224

upstream raw materials:

(2S,5R)-tert-butyl-2-(4-aminobenzyl)-5-((R)-((tert-butyldimethylsilyl) oxy)(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate

4-methoxybenzyl ((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(6-chloropyridin-3-yl)-6-(4-nitrophenyl)hex-5-yn-2-yl)carbamate

4-methoxybenzyl ((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(6-chloropyridin-3-yl)-6-(4-nitrophenyl)-5-oxohexan-2-yl)carbamate

5-((R)-((tert-butyldimethylsilyl)oxy)((2R,5S)-5-(4-nitrobenzyl)pyrrolidin-2-yl)methyl)-2-chloropyridine

Downstream raw materials:

tert-butyl (2S,5R)-2-(4-amino-3-bromobenzyl)-5-[(R)-hydroxy(pyridin-3-yl)methyl]pyrrolidine-1-carboxylate

N-(4-(((2S,5R)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidin-2-yl)methyl)phenyl)-2-(1H-pyrazol-1-yl)acetamide trifluoroacetic acid salt

(S)-N-(4-(((2S,5R)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidin-2-yl)methyl)phenyl)-2-(1H-pyrazol-1-yl)propanamide trifluoroacetic acid salt

C₂₉H₃₅N₅O₄