(1'S,3S,4R,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]heptan]-2-one

Base Information

• Chemical Name: (1'S,3S,4R,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]heptan]-2-one
• CAS No.: 1417817-91-4
• Molecular Formula: C₂₂H₂₃NO
• Molecular Weight: 317.431
• Mol file: 1417817-91-4.mol

Synonyms:(1'S,3S,4R,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]heptan]-2-one

Chemical Property of (1'S,3S,4R,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]heptan]-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S,3S,4R,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]heptan]-2-one

There total 4 articles about (1'S,3S,4R,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]heptan]-2-one 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%

(+)-(1S,2R,4R)-bicyclo<2.2.1>heptane-2-carboxylic acid (2566-59-8) + (E)-N-benzylidenebenzylamine (27845-50-7) → (1'S,3S,4R,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]heptan]-2-one (1417817-91-4) + (1'S,3R,4S,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]heptan]-2-one (1417817-93-6) + 1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]heptan]-2-one (1417817-95-8) + 1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]heptan]-2-one (1417817-96-9)

Guidance literature:

(+)-(1S,2R,4R)-bicyclo<2.2.1>heptane-2-carboxylic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at -5 - 20 ℃; for 4h; Inert atmosphere;

With triethylamine; In toluene; at 0 ℃; for 0.5h;

(E)-N-benzylidenebenzylamine; In toluene; at 90 ℃; for 20.5h; Overall yield = 94 %; diastereoselective reaction; Reflux;

DOI:10.1016/j.tet.2012.11.048

Reference yield:

(1'R,3S,4R,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]hept[5]en]-2-one (1417817-60-7) → (1'S,3S,4R,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]heptan]-2-one (1417817-91-4)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethyl acetate; at 20 ℃;

DOI:10.1016/j.tet.2012.11.048

Reference yield:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1'S,3S,4R,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]heptan]-2-one (1417817-91-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: (S)-o-tol-Corey-Bakshi-Shibata catalyst / dichloromethane / -20 °C

2.1: water; sodium hydroxide / 50 °C

3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 4 h / -5 - 20 °C / Inert atmosphere

3.2: 0.5 h / 0 °C

3.3: 20.5 h / 90 °C / Reflux

4.1: palladium on activated charcoal; hydrogen / ethyl acetate / 20 °C

With (S)-o-tol-Corey-Bakshi-Shibata catalyst; oxalyl dichloride; palladium on activated charcoal; water; hydrogen; N,N-dimethyl-formamide; sodium hydroxide; In dichloromethane; ethyl acetate; 1.1: |Diels-Alder Cycloaddition / 3.3: |Staudinger Ketene Cycloaddition;

DOI:10.1016/j.tet.2012.11.048

upstream raw materials:

cyclopenta-1,3-diene

(+)-(1S,2R,4R)-bicyclo<2.2.1>heptane-2-carboxylic acid

(E)-N-benzylidenebenzylamine

(1'R,3S,4R,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]hept[5]en]-2-one