3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester Chemical Properties

Melting point:

63-67℃

Boiling point:

238.6±50.0 °C(Predicted)

Density 

1.01±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

form 

Solid

color 

White to off-white

Water Solubility 

Slightly soluble in water.

Sensitive 

Moisture Sensitive

InChI

InChI=1S/C11H19BO3/c1-10(2)11(3,4)15-12(14-10)9-5-7-13-8-6-9/h5H,6-8H2,1-4H3

InChIKey

DOSGEBYQRMBTGS-UHFFFAOYSA-N

SMILES

C1OCC=C(B2OC(C)(C)C(C)(C)O2)C1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

20-35

WGK Germany 

3

HS Code 

29349990

3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester Usage And Synthesis

Uses

It plays an important role as intermediate for organic synthesis agrochemical, pharmaceutical and dyestuff field.

Uses

3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester can be used:

• To prepare 1,2-dihydro-2-oxopyridine based endocannabinoid system (ECS) modulators.
• As an intermediate in the synthesis of embryonic ectoderm development (EED) inhibitors.
• To prepare pyrrolotriazine based IRAK4 inhibitors.

Synthesis

To a 250 mL round-bottomed flask, a solution of 3,6-dihydro-2H-pyran-4-trifluoromethanesulfonate (2.7 g, 11.6 mmol), PdCl2(dppf) (440 mg, 0.6 mmol), and potassium acetate (3 g, 36 mmol) was added to a solution of dioxane (20 mL), which was subsequently displaced three times with argon to remove air. The reaction mixture was stirred at 80 °C overnight. Upon completion of the reaction, it was cooled to room temperature and filtered through a short column containing diatomaceous earth to remove solid impurities. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (eluent: 10% dichloromethane solution of hexane) to give the final white solid product 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester (2 g, 81% yield).

References

[1] Patent: WO2008/153858, 2008, A1. Location in patent: Page/Page column 307
[2] Patent: US2012/316147, 2012, A1. Location in patent: Page/Page column 32
[3] Patent: WO2012/168350, 2012, A1. Location in patent: Page/Page column 76; 77
[4] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 7, p. 666 - 670
[5] Patent: US2008/318935, 2008, A1. Location in patent: Page/Page column 65

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