(+/-)-methyl 8-methyl-6-oxo-3-(p-tolyl)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate

Base Information

• Chemical Name: (+/-)-methyl 8-methyl-6-oxo-3-(p-tolyl)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
• CAS No.: 297772-67-9
• Molecular Formula: C₁₇H₁₉NO₃
• Molecular Weight: 285.343
• Mol file: 297772-67-9.mol

Synonyms:(+/-)-methyl 8-methyl-6-oxo-3-(p-tolyl)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate

Chemical Property of (+/-)-methyl 8-methyl-6-oxo-3-(p-tolyl)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-methyl 8-methyl-6-oxo-3-(p-tolyl)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate

There total 6 articles about (+/-)-methyl 8-methyl-6-oxo-3-(p-tolyl)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate 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: 97.0%

(+/-)-methyl 6β-hydroxy-8-methyl-3-(p-tolyl)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate → (+/-)-methyl 8-methyl-6-oxo-3-(p-tolyl)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate (297772-67-9)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1021/jm000141b

Reference yield:

4-methylphenylboronic acid (5720-05-8) → (+/-)-methyl 8-methyl-6-oxo-3-(p-tolyl)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate (297772-67-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / LiCl; tris(dibenzylideneacetone)dipalladium⁽⁰⁾; aq. Na₂CO₃ / 1,2-dimethoxy-ethane / 1 h / Heating

2: 97 percent / n-Bu₄NF / tetrahydrofuran / 12 h / 20 °C

3: 97 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium carbonate; dimethyl sulfoxide; lithium chloride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 3: Swern oxidation;

DOI:10.1021/jm000141b

Reference yield:

(1R,5R,6S)-6-Hydroxy-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one (60873-19-0) → (+/-)-methyl 8-methyl-6-oxo-3-(p-tolyl)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate (297772-67-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 95 percent / imidazole / dimethylformamide / 32 h / 20 °C

2.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C

2.2: 28 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C

3.2: 62 percent / tetrahydrofuran / -78 - 20 °C

4.1: 97 percent / LiCl; tris(dibenzylideneacetone)dipalladium⁽⁰⁾; aq. Na₂CO₃ / 1,2-dimethoxy-ethane / 1 h / Heating

5.1: 97 percent / n-Bu₄NF / tetrahydrofuran / 12 h / 20 °C

6.1: 97 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

With 1H-imidazole; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium carbonate; dimethyl sulfoxide; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; N,N-dimethyl-formamide; 6.1: Swern oxidation;

DOI:10.1021/jm000141b

upstream raw materials:

4-methylphenylboronic acid

(1R,5R,6S)-6-Hydroxy-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one