N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester Chemical Properties

Melting point:

114.0 to 118.0 °C

Boiling point:

348.0±52.0 °C(Predicted)

Density 

1.05±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Sparingly), Dichloromethane (Sparingly), DMSO (Slightly)

pka

-1.21±0.40(Predicted)

form 

Solid

color 

white to off-white

Water Solubility 

Soluble in most organic solvents. Insoluble in water.

InChI

InChI=1S/C16H28BNO4/c1-14(2,3)20-13(19)18-10-8-12(9-11-18)17-21-15(4,5)16(6,7)22-17/h8H,9-11H2,1-7H3

InChIKey

VVDCRJGWILREQH-UHFFFAOYSA-N

SMILES

C1N(C(OC(C)(C)C)=O)CC=C(B2OC(C)(C)C(C)(C)O2)C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37-60

WGK Germany 

3

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29349990

N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester Usage And Synthesis

Chemical Properties

off-white powder

Uses

Reagent used for suzuki-Miyaura cross-coupling using palladium phosphine catalyst, palladium-catalyzed ligand-controlled regioselective Suzuki coupling, wrenchnolol derivative optimized for gene activation in cells. Also used in Preparation of several enzymatic inhibitors and receptor ligands, orally active anaplastic lymphoma kinase inhibitors and oxazolecarboxamides as diacylglycerol acyltransferase-1 inhibitors for treatment of obesity and diabetes.

Uses

N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester is an intermediate for organic synthesis and pharmaceutical research and development, and can be used for suzuki reaction.

Synthesis

The general procedure for the synthesis of 1,2,3,6-tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine from tert-butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate and bipinacolato pinacol ester was carried out as follows: to a dry reaction flask, bis(pinacolato)diboron ( 3.37 g, 13.28 mmol), potassium acetate (KOAc, 3.58 g, 36.46 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (PDCL2DPPF, 0.27 g, 0.36 mmol), and 1,1'-bis(diphenylphosphino)ferrocene (dppf, 0.2 g, 0.36 mmol) to a dry reaction flask, and the reaction system was subsequently flushed with argon to flush the reaction system. A solution of tert-butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate (4.00 g, 12.07 mmol) in dioxane (35 mL) was added, and the reaction mixture was stirred at 80 °C overnight. After completion of the reaction, it was cooled to room temperature, diluted with water (50 mL) and extracted with ethyl acetate (EtOAc, 50 mL). The organic layer was separated, washed with saturated saline (50 mL), dried over anhydrous magnesium sulfate (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the crude product was purified by fast column chromatography (eluent ratio of 9:1 hexane:ethyl acetate) to give the target product as a white solid (4.5 g, 100% yield).

References

[1] Patent: WO2004/58727, 2004, A1. Location in patent: Page 53-54
[2] Patent: WO2014/100501, 2014, A1. Location in patent: Paragraph 00727; 00728
[3] Patent: WO2015/200534, A2. Location in patent: Paragraph 00297; 00586; 00643
[3] Patent: , 2015, . Location in patent: Paragraph 00297; 00586; 00643
[5] Patent: WO2008/88881, 2008, A1. Location in patent: Page/Page column 59-60

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