2-Methylpiperidine → HCID 57666047, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methyl-2-(5-trifluoromethanesulfonyloxy-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester, 1g (63 mg, 0.12 mmol) in toluene (1 mL) in a sealed tube was added racemic-2-(di-t-butylphosphino)-1,1′-binaphthyl (48 mg, 0.12 mmol), Pd(O AC)2 (27 mg, 0.12 mmol), 2-methyl-piperidine (0.020 mL, 0.17 mmol). The system was flushed with nitrogen. To this was added NaOtBu (14 mg, 0.14 mmol) and heated to 100° C. for 10 minutes. The reaction was cooled to room temperature. To this was added another portion of Pd(OAC)2 (27 mg, 0.12 mmol), 2-methyl-piperidine (0. 020 mL, 0.17 mmol) and NaOtBu (14 mg, 0.14 mmol). The system was heated to 100° C. for 5 minutes, cooled to room temperature and quenched by slow addition of water. The mixture was extracted with EtOAc (3×20 mL). The organic phase was washed with saturated NaHCO3 solution and brine. The organic fraction was dried (MgSO4) and concentrated in vacuo. The crude mixture was purified by ISCO column chromatography to obtain 4-methyl-2-[5-(2-methyl-piperidin-1-yl)-4′-trifluoromethyl-biphenyl-3-yl]-pentanoic acid ethyl ester. Calcd for C27H34F3NO2 (M+H) 462.56, Found 462.3.

Provenance & Evidence