1-BOC-3-[(1,1-DIMETHYLETHYL)DIMETHYLSILYLOXYMETHYL]-PIPERIDIN-4-ONE

Base Information

• Chemical Name: 1-BOC-3-[(1,1-DIMETHYLETHYL)DIMETHYLSILYLOXYMETHYL]-PIPERIDIN-4-ONE
• CAS No.: 849767-21-1
• Molecular Formula: C17H33NO4Si
• Molecular Weight: 343.53400
• Mol file: 849767-21-1.mol

Synonyms:tert-butyl 3-((tert-butyldimethylsilyloxy)methyl)-4-oxopiperidine-1-carboxylate;

Chemical Property of 1-BOC-3-[(1,1-DIMETHYLETHYL)DIMETHYLSILYLOXYMETHYL]-PIPERIDIN-4-ONE

Chemical Property:

• PSA: 55.84000
• LogP: 3.77220
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

1-Boc-3-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-piperidin-4-one 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-BOC-3-[(1,1-DIMETHYLETHYL)DIMETHYLSILYLOXYMETHYL]-PIPERIDIN-4-ONE

There total 7 articles about 1-BOC-3-[(1,1-DIMETHYLETHYL)DIMETHYLSILYLOXYMETHYL]-PIPERIDIN-4-ONE 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: 97.0%

tert-butyl 3-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxy-piperidine-1-carboxylate (849767-20-0) → tert-butyl 3-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-oxo-piperidine-1-carboxylate (849767-21-1)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1016/j.bmcl.2005.01.016

Reference yield:

tert-butyl 4-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate (849767-19-7) → tert-butyl 3-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-oxo-piperidine-1-carboxylate (849767-21-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / Et₃N; DMAP / CH₂Cl₂

2: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

With dmap; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 2: Swern oxidation;

DOI:10.1016/j.bmcl.2005.01.016

Reference yield:

methyl 1-tert-butoxycarbonyl-4-oxo-3-piperidinecarboxylate (161491-24-3) → tert-butyl 3-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-oxo-piperidine-1-carboxylate (849767-21-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / NaBH₄ / methanol; tetrahydrofuran

2: 83 percent / Et₃N; DMAP / CH₂Cl₂

3: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

With dmap; sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 3: Swern oxidation;

DOI:10.1016/j.bmcl.2005.01.016

upstream raw materials:

tert-butyl 3-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxy-piperidine-1-carboxylate

di-tert-butyl dicarbonate

methyl 4-oxo-3-piperidinecarboxylate hydrochloride

methyl 1-tert-butoxycarbonyl-4-oxo-3-piperidinecarboxylate

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