1-(2-[(tert-butyldimethylsilyl)oxy]benzyl)pyrrolidine

Base Information

• Chemical Name: 1-(2-[(tert-butyldimethylsilyl)oxy]benzyl)pyrrolidine
• CAS No.: 1354018-86-2
• Molecular Formula: C₁₇H₂₉NOSi
• Molecular Weight: 291.509
• Mol file: 1354018-86-2.mol

Synonyms:1-(2-[(tert-butyldimethylsilyl)oxy]benzyl)pyrrolidine

Chemical Property of 1-(2-[(tert-butyldimethylsilyl)oxy]benzyl)pyrrolidine

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of 1-(2-[(tert-butyldimethylsilyl)oxy]benzyl)pyrrolidine

There total 5 articles about 1-(2-[(tert-butyldimethylsilyl)oxy]benzyl)pyrrolidine 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: 45.0%

pyrrolidine (123-75-1) + 2-(tert-butyldimethylsilyloxy)benzyl nitrate (1354018-44-2) → 1-(2-[(tert-butyldimethylsilyl)oxy]benzyl)pyrrolidine (1354018-86-2)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 31h; Inert atmosphere; Reflux;

DOI:10.1021/ol203196n

Reference yield:

{2-[(tert-butyldimethylsilyl)oxy]phenyl}methanol (96013-79-5) → 1-(2-[(tert-butyldimethylsilyl)oxy]benzyl)pyrrolidine (1354018-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride; silver nitrate / tetrahydrofuran / 25 °C / Inert atmosphere

2: tetrahydrofuran / 31 h / -78 °C / Inert atmosphere; Reflux

With thionyl chloride; silver nitrate; In tetrahydrofuran;

DOI:10.1021/ol203196n

Reference yield:

salicylaldehyde (90-02-8) → 1-(2-[(tert-butyldimethylsilyl)oxy]benzyl)pyrrolidine (1354018-86-2)

Guidance literature:

Multi-step reaction with 4 steps

1: dmap; triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

2: sodium tetrahydroborate / methanol / 6 h / 20 °C / Inert atmosphere

3: thionyl chloride; silver nitrate / tetrahydrofuran / 25 °C / Inert atmosphere

4: tetrahydrofuran / 31 h / -78 °C / Inert atmosphere; Reflux

With dmap; sodium tetrahydroborate; thionyl chloride; silver nitrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol203196n

upstream raw materials:

pyrrolidine

2-(tert-butyldimethylsilyloxy)benzyl nitrate

{2-[(tert-butyldimethylsilyl)oxy]phenyl}methanol

salicylaldehyde