2-(benzyldimethylsilyl)methyl-1-p-toluenesulfonylpyrrolidine

Base Information

• Chemical Name: 2-(benzyldimethylsilyl)methyl-1-p-toluenesulfonylpyrrolidine
• CAS No.: 259874-81-2
• Molecular Formula: C₂₁H₂₉NO₂SSi
• Molecular Weight: 387.618
• Mol file: 259874-81-2.mol

Synonyms:2-(benzyldimethylsilyl)methyl-1-p-toluenesulfonylpyrrolidine

Chemical Property of 2-(benzyldimethylsilyl)methyl-1-p-toluenesulfonylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(benzyldimethylsilyl)methyl-1-p-toluenesulfonylpyrrolidine

There total 8 articles about 2-(benzyldimethylsilyl)methyl-1-p-toluenesulfonylpyrrolidine 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: 96.0%

N-((Z)-5-benzyldimethylsilyl-4-pentenyl)-p-toluenesulfonamide (259874-52-7) → N-tosyl-(4-pentenyl)amine (81097-24-7) + 2-(benzyldimethylsilyl)methyl-1-p-toluenesulfonylpyrrolidine (259874-81-2)

Guidance literature:

With toluene-4-sulfonic acid; In chloroform; at 60 ℃; for 3.3h;

DOI:10.1021/ol991341o

Reference yield:

5-(benzyldimethylsilyl)-1-(tetrahydropyran-2′-yloxy)pent-4-yne (259874-44-7) → 2-(benzyldimethylsilyl)methyl-1-p-toluenesulfonylpyrrolidine (259874-81-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 65 percent / DIBALH / diethyl ether; hexane / 40 h / 20 °C

2: 92 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3: 99 percent / NH₂OH*HCl; Na₂CO₃ / H₂O / 1 h / 20 °C

4: 84 percent / LAH / diethyl ether; diisopropyl ether / 24 h / 55 °C

5: 96 percent / Et₃N / CH₂Cl₂ / 1 h

6: 93 percent / TiCl₄ / CHCl₃ / 3.3 h / 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; hydroxylamine hydrochloride; titanium tetrachloride; diisobutylaluminium hydride; sodium carbonate; dimethyl sulfoxide; triethylamine; In diethyl ether; hexane; dichloromethane; chloroform; di-isopropyl ether; water; 1: Reduction / 2: Oxidation / 3: Substitution / 4: Reduction / 5: Acylation / 6: desilylation;

DOI:10.1021/ol991341o

Reference yield:

(Z)-5-benzyldimethylsilyl-4-pentenal (259874-48-1) → 2-(benzyldimethylsilyl)methyl-1-p-toluenesulfonylpyrrolidine (259874-81-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / NH₂OH*HCl; Na₂CO₃ / H₂O / 1 h / 20 °C

2: 84 percent / LAH / diethyl ether; diisopropyl ether / 24 h / 55 °C

3: 96 percent / Et₃N / CH₂Cl₂ / 1 h

4: 93 percent / TiCl₄ / CHCl₃ / 3.3 h / 20 °C

With lithium aluminium tetrahydride; hydroxylamine hydrochloride; titanium tetrachloride; sodium carbonate; triethylamine; In diethyl ether; dichloromethane; chloroform; di-isopropyl ether; water; 1: Substitution / 2: Reduction / 3: Acylation / 4: desilylation;

DOI:10.1021/ol991341o

upstream raw materials:

N-((Z)-5-benzyldimethylsilyl-4-pentenyl)-p-toluenesulfonamide

5-(benzyldimethylsilyl)-1-(tetrahydropyran-2′-yloxy)pent-4-yne

(Z)-5-benzyldimethylsilyl-4-pentenal

(4Z)-5-benzyldimethylsilyl-4-pentenal oxime

Downstream raw materials:

(RS)-[1-(toluene-4-sulfonyl)-pyrrolidine-2-yl]-methanol