(1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine]

Base Information

• Chemical Name: (1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine]
• CAS No.: 635298-66-7
• Molecular Formula: C₂₅H₂₉N₃O₂
• Molecular Weight: 403.524
• Mol file: 635298-66-7.mol

Synonyms:(1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine]

Chemical Property of (1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine]

There total 2 articles about (1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine] 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: 43.0%

(R,R)-1,2-diphenylethylenediamine (35132-20-8) + (1RS,4RS)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2-one → (1S,4S,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine] (636999-35-4) + (1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine] (635298-66-7)

Guidance literature:

In dichloromethane; for 24h;

DOI:10.1016/j.tetasy.2003.08.021

Reference yield:

(1S,4R)-5-Oxo-6-(toluene-4-sulfonyl)-7-aza-bicyclo[2.2.1]hept-2-ene-7-carboxylic acid tert-butyl ester → (1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine] (635298-66-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / SmI₂ / tetrahydrofuran; methanol / 0.17 h / -78 °C

2: 43 percent / CH₂Cl₂ / 24 h

With samarium diiodide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tetasy.2003.08.021

Reference yield: 96.0%

(1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine] (635298-66-7) → (R,R)-1,2-diphenylethylenediamine (35132-20-8) + (1R,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2-one (635298-67-8)

Guidance literature:

With phosphoric acid; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetasy.2003.08.021

upstream raw materials:

(R,R)-1,2-diphenylethylenediamine

Downstream raw materials:

(R,R)-1,2-diphenylethylenediamine

(1R,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2-one

(-)-(1R,4S)-tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate