Dichloromethane → Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

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Reaction Conditions

Reaction Steps

A mixture of tert-butyl 4{[(trifluoromethyl)sulfonyl]oxy}-1,2,3,6-tetrahydro-1-pyridinecarboxylate (1.8 g, 2.42 mmol), pinacol diboron (1.4 g, 5.44 mmol), potassium acetate (1.6 g, 16.32 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (0.27 g, 0.33 mmol) in N,N-dimethylformamide (30 mL) was heated in an 85° C. oil bath for 17 hours. The solvent was evaporated under reduced pressure then the residue was triturated with dichloromethane (30 mL). The mixture was filtered through a bed of diatomaceous earth then the solvents were evaporated under reduced pressure and the residue purified by flash chromatography on silica gel with heptane/ethyl acetate (8:2) as an eluent. The appropriate fractions were concentrated under reduced pressure to provide the title compound as a crystalline solid (0.87 g, 52%); TLC RF 0.44, heptane/ethyl acetate (8:2), visualized by PMA/heat, Silica Gel 60 F254 plates; 1H NMR (CDCl3, 400 MHz) δ 6.46 (m, 1H), 3.94 (m, 2H), 3.43 (m, 2H), 2.21 (m, 2H), 1.45 (s, 9H), 1.26 (s, 12H)

Provenance & Evidence