(1S,5S,6R,R_S)-N-methyl-4β-phenyl-6β-(p-tolylsulfinyl)-3α-p-tolyl-8-azabicyclo<3.2.1>octan-2-one

Base Information

• Chemical Name: (1S,5S,6R,R_S)-N-methyl-4β-phenyl-6β-(p-tolylsulfinyl)-3α-p-tolyl-8-azabicyclo<3.2.1>octan-2-one
• CAS No.: 208989-17-7
• Molecular Formula: C₂₈H₂₉NO₂S
• Molecular Weight: 443.61

Synonyms:(1S,5S,6R,R_S)-N-methyl-4β-phenyl-6β-(p-tolylsulfinyl)-3α-p-tolyl-8-azabicyclo<3.2.1>octan-2-one

Chemical Property of (1S,5S,6R,R_S)-N-methyl-4β-phenyl-6β-(p-tolylsulfinyl)-3α-p-tolyl-8-azabicyclo<3.2.1>octan-2-one

Chemical Property:

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Useful:

Technology Process of (1S,5S,6R,R_S)-N-methyl-4β-phenyl-6β-(p-tolylsulfinyl)-3α-p-tolyl-8-azabicyclo<3.2.1>octan-2-one

There total 3 articles about (1S,5S,6R,R_S)-N-methyl-4β-phenyl-6β-(p-tolylsulfinyl)-3α-p-tolyl-8-azabicyclo<3.2.1>octan-2-one 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) → (1S,5S,6R,RS)-N-methyl-4β-phenyl-6β-(p-tolylsulfinyl)-3α-p-tolyl-8-azabicyclo<3.2.1>octan-2-one (208989-17-7)

Guidance literature:

Multi-step reaction with 2 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

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium fluoride; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; In 1,4-dioxane;

DOI:10.1021/jm9802564

Reference yield:

1-methyl-4-p-tolyl-3-pyridiniumolate (208989-08-6) → (1S,5S,6R,RS)-N-methyl-4β-phenyl-6β-(p-tolylsulfinyl)-3α-p-tolyl-8-azabicyclo<3.2.1>octan-2-one (208989-17-7)

Guidance literature:

Multi-step reaction with 2 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

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium fluoride; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; In 1,4-dioxane;

DOI:10.1021/jm9802564

Reference yield:

phenylmagnesium bromide (100-58-3) + (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) → (1S,5S,6R,RS)-N-methyl-4β-phenyl-6β-(p-tolylsulfinyl)-3α-p-tolyl-8-azabicyclo<3.2.1>octan-2-one (208989-17-7)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium fluoride; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; Yield given; Multistep reaction; 1.) Et₂O, THF, -78 deg C, 1 h, 2.) MeOH, RT, 5 min;

DOI:10.1021/jm9802564

upstream raw materials:

phenylmagnesium bromide

(1S,5S,6R,R_S)-N-methyl-6-(p-tolylsulfinyl)-3-p-tolyl-8-azabicyclo<3.2.1>oct-3-en-2-one

(R)-p-tolyl vinyl sulfoxide

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

Downstream raw materials:

(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

C₂₈H₃₁NO₂S

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

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

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