Methyl Acrylate → (2R)-4-[5-(2-Methoxycarbonyl-vinyl)-3-trifluoromethyl-pyridin-2-yl]-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of (2R)-4-(5-bromo-3-trifluoromethyl-pyridin-2-yl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester from step (c) above (8.48 g, 20 mmol), methyl acrylate (1.9 g, 22 mmol, Aldrich), palladium acetate (49 mg, 2.0 mmol, Aldrich) and benzyltriethyl ammonium chloride (456 mg, 2.0 mmol, Aldrich) in DMF (20 mL) was stirred at 40° C. for 18 h. The reaction mixture was cooled to room temperature, diluted with water (50 mL) and extracted with EtOAc (2×80 mL). The combined organic extracts were washed with brine (40 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography, eluting with 20% EtOAc/hexane to give the title compound as a white solid. MS (ESI, pos. ion) m/e: 430 (M+1).

Provenance & Evidence