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

Base Information

• Chemical Name: (2S,5R)-tert-butyl-2-(4-aminobenzyl)-5-((R)-((tert-butyldimethylsilyl) oxy)(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate
• CAS No.: 1190615-04-3
• Molecular Formula: C₂₈H₄₃N₃O₃Si
• Molecular Weight: 497.753
• Mol file: 1190615-04-3.mol

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

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

There total 12 articles about (2S,5R)-tert-butyl-2-(4-aminobenzyl)-5-((R)-((tert-butyldimethylsilyl) oxy)(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: 76.0%

(2S,5S)-tert-butyl 2-((R)-((tert-butyldimethylsilyl)oxy)(6-chloropyridin-3-yl)methyl)-5-(4-nitrobenzyl)pyrrolidine-1-carboxylate (1190615-05-4) → (2S,5R)-tert-butyl-2-(4-aminobenzyl)-5-((R)-((tert-butyldimethylsilyl) oxy)(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate (1190615-04-3)

Guidance literature:

With hydrogen; potassium acetate; palladium 10% on activated carbon; In ethanol; for 8h; under 2585.81 Torr;

Reference yield:

(R)-2-((S)-(6-chloropyridin-3-yl)((trimethylsilyl)oxy)methyl)hex-5-ynoic acid (1190614-98-2) → (2S,5R)-tert-butyl-2-(4-aminobenzyl)-5-((R)-((tert-butyldimethylsilyl) oxy)(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate (1190615-04-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine; diphenyl phosphoryl azide / toluene / 6 h / 20 °C / Inert atmosphere

1.2: 16 h / 100 °C / Inert atmosphere

2.1: copper(l) iodide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / acetonitrile / 0.25 h / 20 °C / Inert atmosphere

2.2: 15 h / 20 °C / Inert atmosphere

3.1: pyrrolidine / N,N-dimethyl-formamide / 5 h / 80 °C / Inert atmosphere

3.2: 3 h / 20 °C

4.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

5.1: sodium cyanoborohydride / methanol / 6 h / 0 °C / Inert atmosphere

5.2: 0 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

7.1: hydrogen; potassium acetate / palladium 10% on activated carbon / ethanol / 8 h / 2585.81 Torr

With pyrrolidine; copper(l) iodide; diphenyl phosphoryl azide; hydrogen; potassium acetate; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

(S)-4-benzyl-3-((R)-2-((S)-(6-chloropyridin-3-yl)(hydroxy)methyl)hex-5-ynoyl)oxazolidin-2-one (1190614-96-0) → (2S,5R)-tert-butyl-2-(4-aminobenzyl)-5-((R)-((tert-butyldimethylsilyl) oxy)(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate (1190615-04-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 16 h / 0 - 3 °C / Inert atmosphere

2.1: sodium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 18 h / 0 - 5 °C / Inert atmosphere

2.2: 0 - 15 °C

2.3: 0 °C / pH 3

3.1: triethylamine; diphenyl phosphoryl azide / toluene / 6 h / 20 °C / Inert atmosphere

3.2: 16 h / 100 °C / Inert atmosphere

4.1: copper(l) iodide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / acetonitrile / 0.25 h / 20 °C / Inert atmosphere

4.2: 15 h / 20 °C / Inert atmosphere

5.1: pyrrolidine / N,N-dimethyl-formamide / 5 h / 80 °C / Inert atmosphere

5.2: 3 h / 20 °C

6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

7.1: sodium cyanoborohydride / methanol / 6 h / 0 °C / Inert atmosphere

7.2: 0 °C

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

9.1: hydrogen; potassium acetate / palladium 10% on activated carbon / ethanol / 8 h / 2585.81 Torr

With pyrrolidine; 2,6-dimethylpyridine; copper(l) iodide; diphenyl phosphoryl azide; hydrogen; dihydrogen peroxide; potassium acetate; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

(2S,5S)-tert-butyl 2-((R)-((tert-butyldimethylsilyl)oxy)(6-chloropyridin-3-yl)methyl)-5-(4-nitrobenzyl)pyrrolidine-1-carboxylate

(S)-4-benzyl-3-((R)-2-((S)-(6-chloropyridin-3-yl)(hydroxy)methyl)hex-5-ynoyl)oxazolidin-2-one

(S)-4-benzyl-3-((R)-2-((S)-(6-chloropyridin-3-yl)((trimethylsilyl)oxy)methyl)hex-5-ynoyl)oxazolidin-2-one

(R)-2-((S)-(6-chloropyridin-3-yl)((trimethylsilyl)oxy)methyl)hex-5-ynoic acid

Downstream raw materials:

tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(pyridin-3-yl)methyl]-5-(4-{[(2R)-2-pyridin-2-ylpropanoyl]amino}benzyl)pyrrolidine-1-carboxylate

tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(pyridin-3-yl)methyl]-5-(4-{[(2S)-2-pyridin-2-ylpropanoyl]amino}benzyl)pyrrolidine-1-carboxylate

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

(R)-N-(4-(((2S,5R)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide