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

Base Information

Chemical Name:(1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid methoxymethyl-(2-bromophenyl)amide
CAS No.:313948-08-2
Molecular Formula:C₂₅H₂₅BrN₂O₃
Molecular Weight:481.389
Hs Code.:

Synonyms:(1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid methoxymethyl-(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 methoxymethyl-(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 methoxymethyl-(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 methoxymethyl-(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: 73.0%

: 107-30-2
chloromethyl methyl ether

: 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

: 313948-08-2
(1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid methoxymethyl-(2-bromophenyl)amide

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 20 ℃; for 18h;
DOI:10.1021/jo001119t

Reference yield:

: 615-36-1
2-bromoaniline

: 313948-08-2
(1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid methoxymethyl-(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: 73 percent / sodium hydride / tetrahydrofuran; various solvent(s) / 18 h / 20 °C

With palladium diacetate; n-butyllithium; sodium hydride; 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

: 313948-08-2
(1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid methoxymethyl-(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: 73 percent / sodium hydride / tetrahydrofuran; various solvent(s) / 18 h / 20 °C

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