TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE

Base Information

• Chemical Name: TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE
• CAS No.: 885693-20-9
• Molecular Formula: C16H28BNO4
• Molecular Weight: 309.214
• Hs Code.: 2934999090
• Mol file: 885693-20-9.mol

Synonyms:1(2H)-Pyridinecarboxylicacid, 5,6-dihydro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-,1,1-dimethylethyl ester (9CI);5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylicacid tert-butyl ester;

Chemical Property of TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE

Chemical Property:

• Melting Point: 105 °C
• Refractive Index: 1.488
• Boiling Point: 348.007 °C at 760 mmHg
• PKA: -1.17±0.40(Predicted)
• Flash Point: 164.269 °C
• PSA: 48.00000
• Density: 1.055 g/cm³
• LogP: 3.12290
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

98%, ^*data from raw suppliers

1-Boc-5,6-dihydro-2H-pyridine-3-boronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: tert-Butyl 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate is used as a reactant in the synthesis of phosphatidylinositol 3-kinase inhibitors.

Technology Process of TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE

There total 13 articles about TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-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: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride → 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (885693-20-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1002/ejoc.202000346

Reference yield: 73.0%

tert-butyl 3-bromo-5,6-dihydropyridine-1(2H)-carboxylate + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (885693-20-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; Inert atmosphere;

Reference yield: 72.0%

tert-butyl but-3-en-1-yl[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]carbamate → 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (885693-20-9)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.202000977

upstream raw materials:

5-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

bis(pinacol)diborane

3-oxo-piperidine-1-carboxylic acid tert-butyl ester

1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid

Refernces

• 1、 -. "Sodium channel blockers (by machine translation)". Paragraph 0364; 0369-0371. . Retrieved 2020/11/05.
• 2、 -. "Preparation method of N-substituted-tetrahydropyridine-3/4-boric acid/ester". Paragraph 0041-0043. . Retrieved 2020/04/22.