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

Base Information

• Chemical Name: (1S,5S,7R,R_S)-3α-(p-fluorophenyl)-2β-phenyl-7β-(p-tolylsulfinyl)tropane
• CAS No.: 208989-25-7
• Molecular Formula: C₂₇H₂₈FNOS
• Molecular Weight: 433.59
• Mol file: 208989-25-7.mol

Synonyms:(1S,5S,7R,R_S)-3α-(p-fluorophenyl)-2β-phenyl-7β-(p-tolylsulfinyl)tropane

Chemical Property of (1S,5S,7R,R_S)-3α-(p-fluorophenyl)-2β-phenyl-7β-(p-tolylsulfinyl)tropane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5S,7R,R_S)-3α-(p-fluorophenyl)-2β-phenyl-7β-(p-tolylsulfinyl)tropane

There total 7 articles about (1S,5S,7R,R_S)-3α-(p-fluorophenyl)-2β-phenyl-7β-(p-tolylsulfinyl)tropane 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:

Thiocarbonic acid O-[(1S,3R,4R,5S,6R)-3-(4-fluoro-phenyl)-8-methyl-4-phenyl-6-((R)-toluene-4-sulfinyl)-8-aza-bicyclo[3.2.1]oct-2-yl] ester O-phenyl ester → (1S,5S,7R,RS)-3α-(p-fluorophenyl)-2β-phenyl-7β-(p-tolylsulfinyl)tropane (208989-25-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 90 ℃; for 1h; Yield given;

DOI:10.1021/jm9802564

Reference yield:

(R)-p-tolyl vinyl sulfoxide (54828-68-1) → (1S,5S,7R,RS)-3α-(p-fluorophenyl)-2β-phenyl-7β-(p-tolylsulfinyl)tropane (208989-25-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 40 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: 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

5: Bu₃SnH, AIBN / toluene / 1 h / 90 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium fluoride; lithium aluminium tetrahydride; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; toluene;

DOI:10.1021/jm9802564

Reference yield:

4-(p-fluorophenyl)-1-methyl-3-pyridiniumolate (208989-10-0) → (1S,5S,7R,RS)-3α-(p-fluorophenyl)-2β-phenyl-7β-(p-tolylsulfinyl)tropane (208989-25-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 40 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: 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

5: Bu₃SnH, AIBN / toluene / 1 h / 90 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium fluoride; lithium aluminium tetrahydride; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; toluene;

DOI:10.1021/jm9802564

upstream raw materials:

(R)-p-tolyl vinyl sulfoxide

4-(p-fluorophenyl)-1-methyl-3-pyridiniumolate

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

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