(1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid acetyl-(2-bromophenyl)amide

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Chemical Name:(1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid acetyl-(2-bromophenyl)amide
CAS No.:313948-09-3
Molecular Formula:C₂₅H₂₃BrN₂O₃
Molecular Weight:479.373
Hs Code.:

Synonyms:(1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid acetyl-(2-bromophenyl)amide

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Chemical Property of (1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid acetyl-(2-bromophenyl)amide

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Technology Process of (1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid acetyl-(2-bromophenyl)amide

There total 6 articles about (1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid acetyl-(2-bromophenyl)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: 93.0%

: 108-24-7
acetic anhydride

: 247171-16-0
(1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide

: 313948-09-3
(1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid acetyl-(2-bromophenyl)amide

Guidance literature:: With dmap; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 20h;
DOI:10.1021/jo001119t

Reference yield:

: 615-36-1
2-bromoaniline

: 313948-09-3
(1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid acetyl-(2-bromophenyl)amide

Guidance literature:: Multi-step reaction with 4 steps

1: 64 percent / Pd(OAc)2; triphenylphosphine; triethylamine / dimethylformamide / 20 h / 40 °C

2: 66 percent / PCC / CH₂Cl₂ / 17 h / 40 °C

3: 83 percent / n-BuLi / tetrahydrofuran; hexane / 18 h / 70 °C

4: 93 percent / N,N-dimethylaminopyridine; Et₃N / dimethylformamide / 20 h / 20 °C

With dmap; palladium diacetate; n-butyllithium; triethylamine; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 3: Wittig reaction;
DOI:10.1021/jo001119t

Reference yield:

: 199103-44-1
1-benzyl-5-ethoxy-4-hydroxy-3-(buta-2,3-dienyl)-2-pyrrolidinone

: 313948-09-3
(1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid acetyl-(2-bromophenyl)amide

Guidance literature:: Multi-step reaction with 5 steps

1: 42 percent / sodium iodide / 18 h / 85 °C

2: 64 percent / Pd(OAc)2; triphenylphosphine; triethylamine / dimethylformamide / 20 h / 40 °C

3: 66 percent / PCC / CH₂Cl₂ / 17 h / 40 °C

4: 83 percent / n-BuLi / tetrahydrofuran; hexane / 18 h / 70 °C

5: 93 percent / N,N-dimethylaminopyridine; Et₃N / dimethylformamide / 20 h / 20 °C

With dmap; palladium diacetate; n-butyllithium; triethylamine; triphenylphosphine; pyridinium chlorochromate; sodium iodide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 4: Wittig reaction;
DOI:10.1021/jo001119t