5,5-Difluoro-1,3-piperidinedicarboxylic acid tert-butyl ester

Base Information

• Chemical Name: 5,5-Difluoro-1,3-piperidinedicarboxylic acid tert-butyl ester
• CAS No.: 1255666-86-4
• Molecular Formula: C₁₁H₁₇F₂NO₄
• Molecular Weight: 265.257
• Mol file: 1255666-86-4.mol

Synonyms:5,5-Difluoro-1,3-piperidinedicarboxylic acid tert-butyl ester;1-Boc-5,5-difluoro-3-piperidinecarboxylic acid

Chemical Property of 5,5-Difluoro-1,3-piperidinedicarboxylic acid tert-butyl ester

Chemical Property:

• Boiling Point: 356.4±42.0 °C(Predicted)
• PKA: 3.66±0.40(Predicted)
• PSA: 66.84000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 1.90120
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

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

1-(tert-Butoxycarbonyl)-5,5-difluoropiperidine-3-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5,5-Difluoro-1,3-piperidinedicarboxylic acid tert-butyl ester

There total 6 articles about 5,5-Difluoro-1,3-piperidinedicarboxylic 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: 83.0%

1-(tert-butyl) 3-methyl 5,5-difluoropiperidine-1,3-dicarboxylate (1255667-06-1) → 1-(tert-butoxycarbonyl)-5,5-difluoropiperidine-3-carboxylic acid (1255666-86-4)

Guidance literature:

With water; sodium hydroxide; In methanol; at 0 - 20 ℃; Inert atmosphere;

Reference yield:

1-(1,1-dimethylethyl) 3-methyl 5-hydroxy-1,3-piperidinedicarboxylate (1095010-47-1,1246442-45-4) → 1-(tert-butoxycarbonyl)-5,5-difluoropiperidine-3-carboxylic acid (1255666-86-4)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 1 h / -60 °C

2.1: diethylamino-sulfur trifluoride / dichloromethane / -20 °C / Inert atmosphere

3.1: sodium hydroxide; water / methanol / 0 - 20 °C / Inert atmosphere

With oxalyl dichloride; diethylamino-sulfur trifluoride; water; dimethyl sulfoxide; sodium hydroxide; In methanol; dichloromethane;

Reference yield:

1-(tert-butyl) 3-methyl 5-oxopiperidine-1,3-dicarboxylate (1303974-96-0) → 1-(tert-butoxycarbonyl)-5,5-difluoropiperidine-3-carboxylic acid (1255666-86-4)

Guidance literature:

Multi-step reaction with 2 steps

1: diethylamino-sulfur trifluoride / dichloromethane / -20 °C / Inert atmosphere

2: sodium hydroxide; water / methanol / 0 - 20 °C / Inert atmosphere

With diethylamino-sulfur trifluoride; water; sodium hydroxide; In methanol; dichloromethane;

upstream raw materials:

methyl 5-hydroxy-3-pyridinecarboxylate

5-hydroxynicotinic acid

methyl 5-hydroxypiperidine-3-carboxylate

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

Refernces

• 1、 -. "SUBSTITUTED [1,2,4] TRIAZOLO [1,5-A] PYRIMIDIN-7-YL COMPOUNDS AS PDE2 INHIBITORS". . . Retrieved 2015/11/10.