Ethyl N-Boc-4-methylpiperidine-4-carboxylate

Base Information

• Chemical Name: Ethyl N-Boc-4-methylpiperidine-4-carboxylate
• CAS No.: 189442-87-3
• Molecular Formula: C14H25NO4
• Molecular Weight: 271.357
• Hs Code.: 2933399090
• Mol file: 189442-87-3.mol

Synonyms:1,4-Piperidinedicarboxylic acid, 4-methyl-, 1-(1,1-dimethylethyl) 4-ethyl ester;

Chemical Property of Ethyl N-Boc-4-methylpiperidine-4-carboxylate

Chemical Property:

• Vapor Pressure: 0.000175mmHg at 25°C
• Refractive Index: 1.4554
• Boiling Point: 329.651 °C at 760 mmHg
• PKA: -2.20±0.40(Predicted)
• Flash Point: 153.168 °C
• PSA: 55.84000
• Density: 1.055 g/cm³
• LogP: 2.52620
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl N-Boc-4-methylpiperidine-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-37/38-41
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Reactant for synthesis of:Dipeptidyl peptidase-4 inhibitor ABT-279Building blocks for piperazine-based CCR5 antagonists

Technology Process of Ethyl N-Boc-4-methylpiperidine-4-carboxylate

There total 7 articles about Ethyl N-Boc-4-methylpiperidine-4-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: 100.0%

1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (142851-03-4) + methyl iodide (74-88-4) → ethyl tert-butyl 4-methylpiperidine-1,4-dicarboxylate (189442-87-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; for 2.5h; Inert atmosphere;

Reference yield:

methyl iodide (74-88-4) → ethyl tert-butyl 4-methylpiperidine-1,4-dicarboxylate (189442-87-3)

Guidance literature:

1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;

methyl iodide; In tetrahydrofuran; at 20 ℃; for 1h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → ethyl tert-butyl 4-methylpiperidine-1,4-dicarboxylate (189442-87-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / water; tetrahydrofuran / 7 h / 20 °C

2.1: triethylamine / 12 h / 20 °C

3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: -78 - 20 °C

With n-butyllithium; potassium carbonate; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; water;

DOI:10.1021/acs.jmedchem.7b00304

upstream raw materials:

1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

methyl iodide

isonipecotic acid

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

Downstream raw materials:

1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid

4-carbamoyl-4-methylpiperidine-1-carboxylic acid tert-butyl ester

tert-butyl 4-isocyanato-4-methylpiperidine-1-carboxylate

4-methyl-4-{3-methyl-2,5-dioxo-4-[1-(4-trifluoromethylphenyl)ethyl]piperazin-1-yl}piperidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 -. "KINASE ANTAGONISTS AND METHODS FOR MAKING AND USING THEM". Page/Page column 132-133. . Retrieved 2020/02/19.
• 2、 -. "Novel heterocyclic derivative capable of being used as SHP2 inhibitor". Paragraph 0283. . Retrieved 2019/08/30.