(Diethylamino)sulfur trifluoride → Tert-butyl 4-[1-fluoro-3-(6-methylpyridin-2-yl)prop-2-yn-1-yl]piperidine-1-carboxylate

Participants

Reaction Steps

Into a solution of the Compound of Example 39 (300 mg, 0.91 mmol) in anhydrous CH2Cl2 (10 mL) cooled at −78° C. was dropped diethylaminosulfur trifluoride (144 μL, 1.01 mmol). The reaction mixture was kept at the same temperature for 2 h, then warmed up to r.t., quenched with water and extracted with CH2Cl2. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with Petroleum Ether-EtOAc 7:3, affording the title product (140 mg) as an oil.

Provenance & Evidence