Methyl 1-Boc-5-oxo-piperidine-3-carboxylate

Base Information

• Chemical Name: Methyl 1-Boc-5-oxo-piperidine-3-carboxylate
• CAS No.: 1303974-96-0
• Molecular Formula: C12H19NO5
• Molecular Weight: 257.28296
• Mol file: 1303974-96-0.mol

Synonyms:Methyl 1-Boc-5-oxo-piperidine-3-carboxylate;1-(tert-butoxycarbonyl)-3-methyl-5-oxopiperidine-3-carboxylic acid

Chemical Property of Methyl 1-Boc-5-oxo-piperidine-3-carboxylate

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

1-tert-Butyl3-methyl5-oxopiperidine-1,3-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 1-Boc-5-oxo-piperidine-3-carboxylate

There total 7 articles about Methyl 1-Boc-5-oxo-piperidine-3-carboxylate 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: 87.0%

1-(1,1-dimethylethyl) 3-methyl 5-hydroxy-1,3-piperidinedicarboxylate (1095010-47-1,1246442-45-4) → 1-(tert-butyl) 3-methyl 5-oxopiperidine-1,3-dicarboxylate (1303974-96-0)

Guidance literature:

1-(1,1-dimethylethyl) 3-methyl 5-hydroxy-1,3-piperidinedicarboxylate; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.25h;

With triethylamine; In dichloromethane; at -78 - 20 ℃; for 2.5h;

Reference yield: 74.0%

rac-(3R,5S)-[1-(tert-butyl) 3-methyl 5-hydroxypiperidine-1,3-dicarboxylate] (1246442-45-4) → 1-(tert-butyl) 3-methyl 5-oxopiperidine-1,3-dicarboxylate (1303974-96-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 3.25h;

DOI:10.1021/acs.jmedchem.8b01602

Reference yield:

methyl 5-hydroxy-3-pyridinecarboxylate (30766-22-4) → 1-(tert-butyl) 3-methyl 5-oxopiperidine-1,3-dicarboxylate (1303974-96-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium on activated charcoal; hydrogen / acetic acid / 60 °C / 2585.81 Torr

2.1: triethylamine / methanol / 0 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -60 °C / Inert atmosphere

3.2: 1 h / -60 °C

With oxalyl dichloride; palladium on activated charcoal; hydrogen; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; acetic acid;

upstream raw materials:

1-(1,1-dimethylethyl) 3-methyl 5-hydroxy-1,3-piperidinedicarboxylate

methyl 5-hydroxy-3-pyridinecarboxylate

5-hydroxynicotinic acid

methyl 5-hydroxypiperidine-3-carboxylate

Downstream raw materials:

1-(tert-butoxycarbonyl)-5,5-difluoropiperidine-3-carboxylic acid

tert-butyl 3,3-difluoro-5-(hydroxymethyl)piperidine-1-carboxylate

1-(tert-butyl) 3-methyl 5,5-difluoropiperidine-1,3-dicarboxylate