Sodium Carbonate → 4-[3-(4-methyl-piperidin-1-yl)4-nitro-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A flask is charged with 1-[5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2-nitro-phenyl]-4-methyl-piperidine (0.090 g, 0.27 mmol) (as prepared in the previous step), 4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.090 g, 0.27 mmol) (Synthesis, 993, (1991)), LiCl (0.022 g, 0.54 mmol), Pd(PPh3)4 (0.015 g, 5 mol %), 2 M Na2CO3 (0.34 mL), DME (0.80 mL) and heated at 80° C. for 30 min. The reaction was diluted with EtOAc (10 mL) and washed with saturated aqueous NaHCO3 (2×10 mL) and brine (10 mL), and the organic layer dried over Na2SO4 and evaporated. The crude product was eluted from a 10-g SPE cartridge (silica) with 10% EtOAc/hexane to give 0.080 g (74%) of the title compound as a light yellow oil. Mass spectrum (ESI, m/z): Calcd. for C22H31N3O4, 402.2 (M+H), found 402.1.

Provenance & Evidence