N,N-dimethyl-4-((1R,4S,7R)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-en-2-yl)aniline

Base Information

• Chemical Name: N,N-dimethyl-4-((1R,4S,7R)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-en-2-yl)aniline
• CAS No.: 1309435-05-9
• Molecular Formula: C₂₂H₂₅NOS
• Molecular Weight: 351.513

Synonyms:N,N-dimethyl-4-((1R,4S,7R)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-en-2-yl)aniline

Chemical Property of N,N-dimethyl-4-((1R,4S,7R)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-en-2-yl)aniline

Chemical Property:

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Technology Process of N,N-dimethyl-4-((1R,4S,7R)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-en-2-yl)aniline

There total 4 articles about N,N-dimethyl-4-((1R,4S,7R)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-en-2-yl)aniline 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: 28.0%

4-(7-bromobicyclo[2.2.1]hept-2-en-2-yl)-N,N-dimethylaniline + (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate (1517-82-4) → N,N-dimethyl-4-((1R,4S,7R)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-en-2-yl)aniline (1309435-05-9) + N,N-dimethyl-4-((1R,4S,7R)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-en-2-yl)aniline

Guidance literature:

4-(7-bromobicyclo[2.2.1]hept-2-en-2-yl)-N,N-dimethylaniline; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 2h; Inert atmosphere;

With magnesium chloride; In tetrahydrofuran; pentane; at -78 ℃; for 0.5h; Inert atmosphere;

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate; In tetrahydrofuran; pentane; at -78 ℃; for 4h; Inert atmosphere; Resolution of racemate;

DOI:10.1021/ol200841x

Reference yield:

norborn-2-ene (498-66-8) → N,N-dimethyl-4-((1R,4S,7R)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-en-2-yl)aniline (1309435-05-9) + N,N-dimethyl-4-((1R,4S,7R)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-en-2-yl)aniline

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-Bromosuccinimide / water / 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: lanthanum trichloride lithium chloride complex / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.2: 4 h / -78 - 20 °C / Inert atmosphere

3.3: -78 °C / Inert atmosphere

4.1: tert.-butyl lithium / tetrahydrofuran; pentane / 2 h / -78 °C / Inert atmosphere

4.2: 0.5 h / -78 °C / Inert atmosphere

4.3: 4 h / -78 °C / Inert atmosphere; Resolution of racemate

With N-Bromosuccinimide; oxalyl dichloride; lanthanum trichloride lithium chloride complex; tert.-butyl lithium; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; water; pentane; 2.1: Swern oxidation;

DOI:10.1021/ol200841x

Reference yield:

syn-7-bromonorbornene (20047-65-8) → N,N-dimethyl-4-((1R,4S,7R)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-en-2-yl)aniline (1309435-05-9) + N,N-dimethyl-4-((1R,4S,7R)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-en-2-yl)aniline

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: lanthanum trichloride lithium chloride complex / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.2: 4 h / -78 - 20 °C / Inert atmosphere

2.3: -78 °C / Inert atmosphere

3.1: tert.-butyl lithium / tetrahydrofuran; pentane / 2 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

3.3: 4 h / -78 °C / Inert atmosphere; Resolution of racemate

With oxalyl dichloride; lanthanum trichloride lithium chloride complex; tert.-butyl lithium; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; pentane; 1.1: Swern oxidation;

DOI:10.1021/ol200841x

upstream raw materials:

norborn-2-ene

bis(4-(dimethylamino)phenyl)magnesium

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

syn-7-bromonorbornene

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