Boron trifluoride etherate → (2R)-1-{4-[({(1R,2R)-2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]cyclopropyl}methoxy)methyl]phenyl}propan-2-ol

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Reaction Conditions

Reaction Steps

The product of example 54 (step A) (100 mg, 0.2 mmol), was dissolved in THF (2.3 mL), and the solution was cooled to −78° C. under N2. n-Butyl lithium (0.1 mL of a 2.5 M solution in hexane, 0.25 mmol) was added dropwise at 78° C. The solution was stirred at −78° C. for 20 minutes. (R)-propylene oxide (16 mg, 0.028 mmol) and BF3.Et2O (33 mg, 0.23 mmol) were then added. The solution was stirred at −78° C. for 30 minutes, and then at RT for 1 h. The solution was partitioned between water and DCM. The aqueous layer was extracted with DCM. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified via silica gel column chromatography (2/1 hexanes/EtOAc) to provide the title compound. MS (ESI) m/z 410 [M+H]+. GPR119 Human EC50: 11 nM

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