(2R,3R)-2-azido-3-phenyl-4-pentenoic acid (2S-(tert-butyldimethylsilyloxymethyl)pyrrolidinyl) amide

Base Information

• Chemical Name: (2R,3R)-2-azido-3-phenyl-4-pentenoic acid (2S-(tert-butyldimethylsilyloxymethyl)pyrrolidinyl) amide
• CAS No.: 438239-65-7
• Molecular Formula: C₂₂H₃₄N₄O₂Si
• Molecular Weight: 414.623
• Mol file: 438239-65-7.mol

Synonyms:(2R,3R)-2-azido-3-phenyl-4-pentenoic acid (2S-(tert-butyldimethylsilyloxymethyl)pyrrolidinyl) amide

Chemical Property of (2R,3R)-2-azido-3-phenyl-4-pentenoic acid (2S-(tert-butyldimethylsilyloxymethyl)pyrrolidinyl) amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-azido-3-phenyl-4-pentenoic acid (2S-(tert-butyldimethylsilyloxymethyl)pyrrolidinyl) amide

There total 5 articles about (2R,3R)-2-azido-3-phenyl-4-pentenoic acid (2S-(tert-butyldimethylsilyloxymethyl)pyrrolidinyl) amide 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: 91.0%

azidoacetyl fluoride (292067-83-5) + 1-(3-phenyl-2-propenyl)-2(S)-(tert-butyldimethylsiloxymethyl)-pyrrolidine (438239-55-5) → (2R,3R)-2-azido-3-phenyl-4-pentenoic acid (2S-(tert-butyldimethylsilyloxymethyl)pyrrolidinyl) amide (438239-65-7)

Guidance literature:

With trimethylaluminum; potassium carbonate; In n-heptane; dichloromethane; at 0 - 20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)01233-9

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (2R,3R)-2-azido-3-phenyl-4-pentenoic acid (2S-(tert-butyldimethylsilyloxymethyl)pyrrolidinyl) amide (438239-65-7)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / tetrahydrofuran / 0.5 h / 20 °C

2: 0.85 g / Et₃N; Pd₂(dba)3*CHCl₃; PPh₃ / acetonitrile / 2 h / 23 °C

3: 84 percent / DIBALH / diethyl ether; toluene / 0 - 20 °C

4: 1.01 g / Et₃N / dimethylformamide / 12 h / 20 °C

5: 91 percent / K₂CO₃; Me₃Al / CH₂Cl₂; heptane / 0.5 h / 0 - 20 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; trimethylaluminum; diisobutylaluminium hydride; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; n-heptane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 5: aza-Claisen rearrangement;

DOI:10.1016/S0040-4020(01)01233-9

Reference yield:

cinnamyl methanesulfonate → (2R,3R)-2-azido-3-phenyl-4-pentenoic acid (2S-(tert-butyldimethylsilyloxymethyl)pyrrolidinyl) amide (438239-65-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 0.85 g / Et₃N; Pd₂(dba)3*CHCl₃; PPh₃ / acetonitrile / 2 h / 23 °C

2: 84 percent / DIBALH / diethyl ether; toluene / 0 - 20 °C

3: 1.01 g / Et₃N / dimethylformamide / 12 h / 20 °C

4: 91 percent / K₂CO₃; Me₃Al / CH₂Cl₂; heptane / 0.5 h / 0 - 20 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; trimethylaluminum; diisobutylaluminium hydride; potassium carbonate; triethylamine; triphenylphosphine; In diethyl ether; n-heptane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 4: aza-Claisen rearrangement;

DOI:10.1016/S0040-4020(01)01233-9

upstream raw materials:

azidoacetyl fluoride

1-(3-phenyl-2-propenyl)-2(S)-(tert-butyldimethylsiloxymethyl)-pyrrolidine

(2E)-3-phenyl-2-propen-1-ol

(S)-(1-cinnamylpyrrolidin-2-yl)methanol