Triethylamine → tert-Butyl (E)-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)piperidine-1-carboxylate

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Reaction Steps

A solution of tert-butyl 4-(prop-2-ynyl)piperidine-1-carboxylate (0.162 g, 0.725 mmol) synthesized in Example B58, Step 1 in methylene chloride (1 mL) was added with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.139 g, 1.09 mmol) and triethylamine (0.00734 g, 0.0725 mmol), and the mixture was stirred at room temperature. The reaction mixture was added with bis(cyclopentadienyl)zirconium(IV) chloride hydride (0.0281 g, 0.109 mmol), and the mixture was stirred at room temperature for 40 hours. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl (E)-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]piperidine-1-carboxylate (0.132 g, 52%).

Provenance & Evidence