thiocarbonic acid O-[8-methyl-4-phenyl-6-(toluene-4-sulfinyl)-3-p-tolyl-8-aza-bicyclo[3.2.1]oct-2-yl] ester O-phenyl ester

Base Information

• Chemical Name: thiocarbonic acid O-[8-methyl-4-phenyl-6-(toluene-4-sulfinyl)-3-p-tolyl-8-aza-bicyclo[3.2.1]oct-2-yl] ester O-phenyl ester
• CAS No.: 218146-32-8
• Molecular Formula: C₃₅H₃₅NO₃S₂
• Molecular Weight: 581.8

Synonyms:thiocarbonic acid O-[8-methyl-4-phenyl-6-(toluene-4-sulfinyl)-3-p-tolyl-8-aza-bicyclo[3.2.1]oct-2-yl] ester O-phenyl ester

Chemical Property of thiocarbonic acid O-[8-methyl-4-phenyl-6-(toluene-4-sulfinyl)-3-p-tolyl-8-aza-bicyclo[3.2.1]oct-2-yl] ester O-phenyl ester

Chemical Property:

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Technology Process of thiocarbonic acid O-[8-methyl-4-phenyl-6-(toluene-4-sulfinyl)-3-p-tolyl-8-aza-bicyclo[3.2.1]oct-2-yl] ester O-phenyl ester

There total 5 articles about thiocarbonic acid O-[8-methyl-4-phenyl-6-(toluene-4-sulfinyl)-3-p-tolyl-8-aza-bicyclo[3.2.1]oct-2-yl] ester O-phenyl ester 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:

(R)-p-tolyl vinyl sulfoxide (54828-68-1) → thiocarbonic acid O-[8-methyl-4-phenyl-6-(toluene-4-sulfinyl)-3-p-tolyl-8-aza-bicyclo[3.2.1]oct-2-yl] ester O-phenyl ester (218146-32-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 45 percent / dioxane / 20 h / Heating

2: 1.) HMPA, CuBr*Me₂S, Me₃SiCl, 2.) potassium fluoride / 1.) Et₂O, THF, -78 deg C, 1 h, 2.) MeOH, RT, 5 min

3: 92 percent / LiAlH₄ / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature

4: 1.) LDA / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, -78 deg C, 1 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium fluoride; lithium aluminium tetrahydride; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; diethyl ether;

DOI:10.1021/jm9802564

Reference yield:

1-methyl-4-p-tolyl-3-pyridiniumolate (208989-08-6) → thiocarbonic acid O-[8-methyl-4-phenyl-6-(toluene-4-sulfinyl)-3-p-tolyl-8-aza-bicyclo[3.2.1]oct-2-yl] ester O-phenyl ester (218146-32-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 45 percent / dioxane / 20 h / Heating

2: 1.) HMPA, CuBr*Me₂S, Me₃SiCl, 2.) potassium fluoride / 1.) Et₂O, THF, -78 deg C, 1 h, 2.) MeOH, RT, 5 min

3: 92 percent / LiAlH₄ / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature

4: 1.) LDA / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, -78 deg C, 1 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium fluoride; lithium aluminium tetrahydride; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; diethyl ether;

DOI:10.1021/jm9802564

Reference yield:

(1S,5S,6R,RS)-N-methyl-6-(p-tolylsulfinyl)-3-p-tolyl-8-azabicyclo<3.2.1>oct-3-en-2-one (208989-13-3) → thiocarbonic acid O-[8-methyl-4-phenyl-6-(toluene-4-sulfinyl)-3-p-tolyl-8-aza-bicyclo[3.2.1]oct-2-yl] ester O-phenyl ester (218146-32-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) HMPA, CuBr*Me₂S, Me₃SiCl, 2.) potassium fluoride / 1.) Et₂O, THF, -78 deg C, 1 h, 2.) MeOH, RT, 5 min

2: 92 percent / LiAlH₄ / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature

3: 1.) LDA / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, -78 deg C, 1 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium fluoride; lithium aluminium tetrahydride; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jm9802564

upstream raw materials:

phenylcarbonochloridothioate

(1S,3R,4R,5S,6R)-8-Methyl-4-phenyl-6-((R)-toluene-4-sulfinyl)-3-p-tolyl-8-aza-bicyclo[3.2.1]octan-2-ol

(R)-p-tolyl vinyl sulfoxide

1-methyl-4-p-tolyl-3-pyridiniumolate

Downstream raw materials:

(1S,2R,3R,5R,7R)-8-Methyl-2-phenyl-3-p-tolyl-7-p-tolylsulfanyl-8-aza-bicyclo[3.2.1]octane

(1R,5S)-2β-phenyl-3α-p-tolyltropane

(1S,5S,7R,R_S)-2β-phenyl-7β-(p-tolylsulfinyl)-3α-p-tolyltropane

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