syn-8-methyl-3-phenyl-3-aza-endo-tricyclo<3.2.1.0^2,4>oct-anti-8-yl p-toluenesulfonate

Base Information

• Chemical Name: syn-8-methyl-3-phenyl-3-aza-endo-tricyclo<3.2.1.0^2,4>oct-anti-8-yl p-toluenesulfonate
• CAS No.: 83136-14-5
• Molecular Formula: C₂₁H₂₃NO₃S
• Molecular Weight: 369.485

Synonyms:syn-8-methyl-3-phenyl-3-aza-endo-tricyclo<3.2.1.0^2,4>oct-anti-8-yl p-toluenesulfonate

Chemical Property of syn-8-methyl-3-phenyl-3-aza-endo-tricyclo<3.2.1.0^2,4>oct-anti-8-yl p-toluenesulfonate

Chemical Property:

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Technology Process of syn-8-methyl-3-phenyl-3-aza-endo-tricyclo<3.2.1.0^2,4>oct-anti-8-yl p-toluenesulfonate

There total 6 articles about syn-8-methyl-3-phenyl-3-aza-endo-tricyclo<3.2.1.0^2,4>oct-anti-8-yl p-toluenesulfonate 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: 49.0%

p-toluenesulfonyl chloride (98-59-9) + syn-8-methyl-3-phenyl-3-aza-endo-tricyclo<3.2.1.02,4>octan-anti-8-ol (83136-13-4) → syn-8-methyl-3-phenyl-3-aza-endo-tricyclo<3.2.1.02,4>oct-anti-8-yl p-toluenesulfonate (83136-14-5)

Guidance literature:

With n-butyllithium; 1.) THF, hexane, -60 deg C , 10 min, 2.) 0 deg C, 2 h;

DOI:10.1021/ja00387a044

Reference yield:

7,7-dimethoxybicyclo<2.2.1>hept-2-ene (875-04-7) → syn-8-methyl-3-phenyl-3-aza-endo-tricyclo<3.2.1.02,4>oct-anti-8-yl p-toluenesulfonate (83136-14-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / p-toluenesulfonic acid / benzene / Heating

2: 64 percent / 15 h / 50 - 60 °C

3: 44 percent / decahydronaphthalene / 1.5 h / 165 - 170 °C

4: 1.) n-Bu₄NClO₄ / 1.) DMF, electrochemical reduction, 2.) THF, -60 deg C, 10 min, -> 25 deg C, 1 h

5: 49 percent / 1.) n-BuLi / 1.) THF, hexane, -60 deg C , 10 min, 2.) 0 deg C, 2 h

With n-butyllithium; tetrabutylammonium perchlorate; toluene-4-sulfonic acid; In decalin; benzene;

DOI:10.1021/ja00387a044

Reference yield:

7-(2,2,2-tribromoethoxy)-7-methoxybicyclo<2.2.1>hept-2-ene → syn-8-methyl-3-phenyl-3-aza-endo-tricyclo<3.2.1.02,4>oct-anti-8-yl p-toluenesulfonate (83136-14-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / 15 h / 50 - 60 °C

2: 44 percent / decahydronaphthalene / 1.5 h / 165 - 170 °C

3: 1.) n-Bu₄NClO₄ / 1.) DMF, electrochemical reduction, 2.) THF, -60 deg C, 10 min, -> 25 deg C, 1 h

4: 49 percent / 1.) n-BuLi / 1.) THF, hexane, -60 deg C , 10 min, 2.) 0 deg C, 2 h

With n-butyllithium; tetrabutylammonium perchlorate; In decalin;

DOI:10.1021/ja00387a044

upstream raw materials:

p-toluenesulfonyl chloride

syn-8-methyl-3-phenyl-3-aza-endo-tricyclo<3.2.1.0^2,4>octan-anti-8-ol

7,7-dimethoxybicyclo<2.2.1>hept-2-ene

3-phenyl-8-(2,2,2-tribromoethoxy)-8-methoxy-3-aza-endo-tricyclo<3.2.1.0^2,4>octane

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