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

Base Information

• Chemical Name: 5-((R)-((tert-butyldimethylsilyl)oxy)((2R,5S)-5-(4-nitrobenzyl)pyrrolidin-2-yl)methyl)-2-chloropyridine
• CAS No.: 1190614-99-3
• Molecular Formula: C₂₃H₃₂ClN₃O₃Si
• Molecular Weight: 462.064
• Mol file: 1190614-99-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about 5-((R)-((tert-butyldimethylsilyl)oxy)((2R,5S)-5-(4-nitrobenzyl)pyrrolidin-2-yl)methyl)-2-chloropyridine 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: 50.0%

5-{(R)-{[tert-butyl(dimethyl)silyl]oxy}[(2R)-5-(4-nitrobenzyl)-3,4-dihydro-2H-pyrrol-2-yl]methyl}-2-chloropyridine (1190615-03-2) → 5-((R)-((tert-butyldimethylsilyl)oxy)((2R,5S)-5-(4-nitrobenzyl)pyrrolidin-2-yl)methyl)-2-chloropyridine (1190614-99-3) + 5-{(R)-{[tert-butyl(dimethyl)silyl]oxy}[(2R,5R)-5-(4-nitrobenzyl)pyrrolidin-2-yl]methyl}-2-chloropyridine (1190615-00-9)

Guidance literature:

5-{(R)-{[tert-butyl(dimethyl)silyl]oxy}[(2R)-5-(4-nitrobenzyl)-3,4-dihydro-2H-pyrrol-2-yl]methyl}-2-chloropyridine; With sodium cyanoborohydride; In methanol; at 0 ℃; for 6h; Inert atmosphere;

With water; In methanol; at 0 ℃;

Reference yield:

C25H29ClN2O4Si → 5-((R)-((tert-butyldimethylsilyl)oxy)((2R,5S)-5-(4-nitrobenzyl)pyrrolidin-2-yl)methyl)-2-chloropyridine (1190614-99-3)

Guidance literature:

Multi-step reaction with 8 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

With pyrrolidine; 2,6-dimethylpyridine; copper(l) iodide; diphenyl phosphoryl azide; t-butyldimethylsiyl triflate; C₃₄H₂₉Cl₂FeP₂Pd⁽¹⁺⁾; dihydrogen peroxide; sodium tris(acetoxy)borohydride; triethylamine; 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:

6-chloronicotinylaldehyde (23100-12-1) → 5-((R)-((tert-butyldimethylsilyl)oxy)((2R,5S)-5-(4-nitrobenzyl)pyrrolidin-2-yl)methyl)-2-chloropyridine (1190614-99-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: triethylamine; magnesium chloride / ethyl acetate / 72 h / 25 °C / Inert atmosphere

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

3.1: 2,6-dimethylpyridine; t-butyldimethylsiyl triflate / dichloromethane / 0 - 25 °C / Inert atmosphere

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

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

5.2: 13 h / 80 - 110 °C / Inert atmosphere

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

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

7.2: 3 h / Inert atmosphere

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

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

With pyrrolidine; 2,6-dimethylpyridine; copper(l) iodide; diphenyl phosphoryl azide; t-butyldimethylsiyl triflate; C₃₄H₂₉Cl₂FeP₂Pd⁽¹⁺⁾; dihydrogen peroxide; sodium tris(acetoxy)borohydride; triethylamine; trifluoroacetic acid; magnesium chloride; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 1.1: |Aldol Condensation / 5.1: |Curtius Rearrangement / 5.2: |Curtius Rearrangement / 6.1: |Sonogashira Cross-Coupling;

DOI:10.1021/jm4017224

upstream raw materials:

5-{(R)-{[tert-butyl(dimethyl)silyl]oxy}[(2R)-5-(4-nitrobenzyl)-3,4-dihydro-2H-pyrrol-2-yl]methyl}-2-chloropyridine

(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:

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

C₃₄H₄₃N₅O₆S