1,3-Piperidinedicarboxylic acid, 5-hydroxy-, 1-(1,1-dimethylethyl) 3-methyl ester

Base Information

• Chemical Name: 1,3-Piperidinedicarboxylic acid, 5-hydroxy-, 1-(1,1-dimethylethyl) 3-methyl ester
• CAS No.: 1095010-47-1
• Molecular Formula: C12H21NO5
• Molecular Weight: 259.302
• Hs Code.: 2933399090
• Mol file: 1095010-47-1.mol

Synonyms:1-tert-Butyl 3-methyl 5-hydroxypiperidine-1,3-dicarboxylate;O1-tert-Butyl O3-methyl 5-hydroxypiperidine-1,3-dicarboxylate;Methyl 1-Boc-5-hydroxypiperidine-3-carboxylate;

Chemical Property of 1,3-Piperidinedicarboxylic acid, 5-hydroxy-, 1-(1,1-dimethylethyl) 3-methyl ester

Chemical Property:

• Boiling Point: 352.1 °C at 760 mmHg
• PKA: 14.33±0.40(Predicted)
• Flash Point: 166.8 °C
• PSA: 76.07000
• Density: 1.182 g/cm³
• LogP: 0.71520
• Storage Temp.: 2-8°C

Purity/Quality:

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

1-tert-Butyl3-Methyl5-Hydroxypiperidine-1,3-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1-tert-Butyl 3-Methyl 5-Hydroxypiperidine-1,3-dicarboxylate is an intermediate used in the synthesis of heterocyclylaminopyrazine derivatives for use as CHK-1 inhibitors. It is also used to prepare pyrrolidinylimidazopyridinylpiperidinylmethanone derivatives and analogs for use as diacylglycerol acyltransferase 2 inhibitors.

Technology Process of 1,3-Piperidinedicarboxylic acid, 5-hydroxy-, 1-(1,1-dimethylethyl) 3-methyl ester

There total 5 articles about 1,3-Piperidinedicarboxylic acid, 5-hydroxy-, 1-(1,1-dimethylethyl) 3-methyl 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: 79.0%

1-(tert-butoxycarbonyl)-5-hydroxypiperidine-3-carboxylic acid (1095010-48-2) + diazomethyl-trimethyl-silane (18107-18-1) → 1-(1,1-dimethylethyl) 3-methyl 5-hydroxy-1,3-piperidinedicarboxylate (1095010-47-1,1246442-45-4)

Guidance literature:

In methanol; hexane; toluene; at 0 - 20 ℃; for 1.5h;

Reference yield: 35.0%

di-tert-butyl dicarbonate (24424-99-5) + methyl 5-hydroxypiperidine-3-carboxylate (1095010-44-8) → 1-(1,1-dimethylethyl) 3-methyl 5-hydroxy-1,3-piperidinedicarboxylate (1095010-47-1,1246442-45-4)

Guidance literature:

With triethylamine; In methanol; at 0 - 20 ℃; Inert atmosphere;

Reference yield:

methyl 5-hydroxy-3-pyridinecarboxylate (30766-22-4) → 1-(1,1-dimethylethyl) 3-methyl 5-hydroxy-1,3-piperidinedicarboxylate (1095010-47-1,1246442-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: platinum(IV) oxide; sulfuric acid; hydrogen / ethanol / 24 h / 20 °C / 2585.81 Torr

2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 18 h / 20 °C

With platinum(IV) oxide; sulfuric acid; hydrogen; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; ethanol;

DOI:10.1016/j.bmcl.2011.03.022

upstream raw materials:

di-tert-butyl dicarbonate

methyl 5-hydroxypiperidine-3-carboxylate

5-bromo-3-pyridine carboxylic acid methyl ester

methyl 5-hydroxy-3-pyridinecarboxylate

Downstream raw materials:

1-(tert-butoxycarbonyl)-5-hydroxypiperidine-3-carboxylic acid

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

1-(tert-butoxycarbonyl)-5-fluoropiperidine-3-carboxylic acid

Refernces

• 1、 -. "SUBSTITUTED [1,2,4] TRIAZOLO [1,5-A] PYRIMIDIN-7-YL COMPOUNDS AS PDE2 INHIBITORS". Page/Page column 52-53. . Retrieved 2015/11/10.
• 2、 DeNinno, Michael P.,Wright, Stephen W.,Visser, Michael S.,Etienne, John B.,Moore, Dianna E.,Olson, Thanh V.,Rocke, Benjamin N.,Andrews, Melissa P.,Zarbo, Cynthia,Millham, Michele L.,Boscoe, Brian P.,Boyer, David D.,Doran, Shawn D.,Houseknecht, Karen L.. "1,5-Substituted nipecotic amides: Selective PDE8 inhibitors displaying diastereomer-dependent microsomal stability". scheme or table. p. 3095 - 3098. Retrieved 2011/06/24.