(1R)-2-carbomethoxy-3-(3,4-dichlorophenyl)-7β-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-2-ene

Base Information

• Chemical Name: (1R)-2-carbomethoxy-3-(3,4-dichlorophenyl)-7β-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-2-ene
• CAS No.: 357924-60-8
• Molecular Formula: C₁₆H₁₇Cl₂NO₃
• Molecular Weight: 342.222

Synonyms:(1R)-2-carbomethoxy-3-(3,4-dichlorophenyl)-7β-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-2-ene

Chemical Property of (1R)-2-carbomethoxy-3-(3,4-dichlorophenyl)-7β-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1R)-2-carbomethoxy-3-(3,4-dichlorophenyl)-7β-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-2-ene

There total 5 articles about (1R)-2-carbomethoxy-3-(3,4-dichlorophenyl)-7β-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-2-ene 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:

(1S,5R,7R)-3-(3,4-Dichloro-phenyl)-7-methoxymethoxy-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ene-2-carboxylic acid methyl ester → (1R)-2-carbomethoxy-3-(3,4-dichlorophenyl)-7β-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-2-ene (357924-60-8)

Guidance literature:

With trimethylsilyl bromide; 4 A molecular sieve; In dichloromethane; at 0 - 22 ℃;

DOI:10.1021/jm0101242

Reference yield:

(1R)-7β-methoxymethoxy-2-methoxycarbonyl-8-methyl-3-oxo-8-azabicyclo[3.2.1]octane → (1R)-2-carbomethoxy-3-(3,4-dichlorophenyl)-7β-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-2-ene (357924-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaN(TMS)2 / tetrahydrofuran / 0.5 h / -70 °C

1.2: tetrahydrofuran / -70 - 22 °C

2.1: LiCl; aq. Na₂CO₃; Pd₂(dba)3 / various solvent(s) / Heating

3.1: TMSBr; 4A molecular sieves / CH₂Cl₂ / 0 - 22 °C

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trimethylsilyl bromide; 4 A molecular sieve; sodium hexamethyldisilazane; sodium carbonate; lithium chloride; In tetrahydrofuran; dichloromethane; 2.1: Suzuki coupling;

DOI:10.1021/jm0101242

Reference yield:

7β-methoxymethoxy-2-methoxycarbonyl-8-methyl-3-oxo-8-azabicyclo[3.2.1]octane → (1R)-2-carbomethoxy-3-(3,4-dichlorophenyl)-7β-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-2-ene (357924-60-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C

1.2: 36 percent / tetrahydrofuran / -78 - 22 °C

2.1: 0.89 g / aq. LiOH / tetrahydrofuran / 3 h / 22 °C

3.1: NaN(TMS)2 / tetrahydrofuran / 0.5 h / -70 °C

3.2: tetrahydrofuran / -70 - 22 °C

4.1: LiCl; aq. Na₂CO₃; Pd₂(dba)3 / various solvent(s) / Heating

5.1: TMSBr; 4A molecular sieves / CH₂Cl₂ / 0 - 22 °C

With lithium hydroxide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trimethylsilyl bromide; 4 A molecular sieve; sodium hexamethyldisilazane; sodium carbonate; lithium chloride; In tetrahydrofuran; dichloromethane; 4.1: Suzuki coupling;

DOI:10.1021/jm0101242

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