4-Toluenesulfonyl chloride → 2-{(1R,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl 4-methylbenzenesulfonate

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Reaction Steps

The title compound was synthesized using 2-{2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanol from Example 2b-S (slow) (41.2 mg, 0.146 mmol) was in 1.46 mL dichloromethane. TEA (0.0408 mL, 0.296 mol), DMAP (1.786 mg, 0.015 mmol) and TsCl (33.5 mg, 0.175 mmol) were sequentially added. The mixture was stirred at room temperature for 3 hour. Another 0.02 mL of TEA, 1 mg of DMAP and 14 mg of TsCl were added. Reaction mixture was stirred at room temperature for 30 min. The mixture was poured in to ice water. The aqueous phase was extracted with ethyl acetate for 3 times. The combined organic layers were washed with water and brine, then dried over Na2SO4 and concentrated. The residue was purified by column chromatography using gradient elution (0 to 50% ethyl acetate in hexane) to give the titled compound.

Provenance & Evidence