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

Base Information

Chemical Name:(1'R,3R,4S,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]hept[5]en]-2-one
CAS No.:1417817-63-0
Molecular Formula:C₂₂H₂₁NO
Molecular Weight:315.415
Hs Code.:

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

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

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

There total 3 articles about (1'R,3R,4S,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]hept[5]en]-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: 45.0%

: 58001-99-3
5-norbornene-2-carboxylic acid

: 27845-50-7
(E)-N-benzylidenebenzylamine

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

: 1417817-63-0
(1'R,3R,4S,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]hept[5]en]-2-one

: 1417817-65-2
(1'R,3R,4R,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]hept[5]en]-2-one

: 1417817-67-4
1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]hept[5]en]-2-one

Guidance literature:: 5-norbornene-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 = 98 %; diastereoselective reaction; Reflux;
DOI:10.1016/j.tet.2012.11.048

Reference yield:

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: 1417817-63-0
(1'R,3R,4S,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]hept[5]en]-2-one

Guidance literature:: Multi-step reaction with 3 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

With (S)-o-tol-Corey-Bakshi-Shibata catalyst; oxalyl dichloride; water; N,N-dimethyl-formamide; sodium hydroxide; In dichloromethane; 1.1: |Diels-Alder Cycloaddition / 3.3: |Staudinger Ketene Cycloaddition;
DOI:10.1016/j.tet.2012.11.048

Reference yield:

: ethyl (1R,2R,4R)-bicyclo[2.2.1]hept-5-ene-2-carboxylate.

: 1417817-63-0
(1'R,3R,4S,4'R)-1-benzyl-4-phenyl-2H-spiro[azetidine-3,2'-bicyclo[2.2.1]hept[5]en]-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: water; sodium hydroxide / 50 °C

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

2.2: 0.5 h / 0 °C

2.3: 20.5 h / 90 °C / Reflux

With oxalyl dichloride; water; N,N-dimethyl-formamide; sodium hydroxide; In dichloromethane; 2.3: |Staudinger Ketene Cycloaddition;
DOI:10.1016/j.tet.2012.11.048