4-Cyano-4-(toluene-4-sulfonyloxyMethyl)-piperidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 4-Cyano-4-(toluene-4-sulfonyloxyMethyl)-piperidine-1-carboxylic acid tert-butyl ester
• CAS No.: 929302-00-1
• Molecular Formula: C19H26N2O5S
• Molecular Weight: 394.492
• Mol file: 929302-00-1.mol

Synonyms:4-Cyano-4-(toluene-4-sulfonyloxyMethyl)-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property of 4-Cyano-4-(toluene-4-sulfonyloxyMethyl)-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property:

• PSA: 105.08000
• LogP: 4.25988

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Cyano-4-(toluene-4-sulfonyloxyMethyl)-piperidine-1-carboxylic acid tert-butyl ester

There total 8 articles about 4-Cyano-4-(toluene-4-sulfonyloxyMethyl)-piperidine-1-carboxylic acid tert-butyl ester 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: 74.0%

tert-butyl 4-cyano-4-(hydroxymethyl) piperidine-1-carboxylate (614730-96-0) + p-toluenesulfonyl chloride (98-59-9) → tert-butyl 4-cyano-4-({[(4-methylphenyl)sulfonyl]oxy}methyl)piperidine-1-carboxylate (929302-00-1)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1016/j.bmcl.2009.11.084

Reference yield:

1-(tert-butyl) 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate (1016258-66-4) → tert-butyl 4-cyano-4-({[(4-methylphenyl)sulfonyl]oxy}methyl)piperidine-1-carboxylate (929302-00-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol / 1.5 h / 0 °C / Inert atmosphere

2: triethylamine; dmap / dichloromethane / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;

Reference yield:

1-tert-butoxycarbonyl-4-cyanopiperidine (91419-52-2) → tert-butyl 4-cyano-4-({[(4-methylphenyl)sulfonyl]oxy}methyl)piperidine-1-carboxylate (929302-00-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 °C

2.1: sodium tetrahydroborate / methanol / 1.5 h / 0 °C / Inert atmosphere

3.1: triethylamine; dmap / dichloromethane / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

tert-butyl 4-cyano-4-(hydroxymethyl) piperidine-1-carboxylate

p-toluenesulfonyl chloride

4-cyanopiperidine

1-tert-butoxycarbonyl-4-cyanopiperidine

Downstream raw materials:

2-benzyl 7-(tert-butyl) 2,7-diazaspiro[3.5]nonane-2,7-dicarboxylate

tert-butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate hydrochloride