Ethyl 4-piperidinecarboxylate → Ethyl 1-{2-[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]ethyl}-4-piperidinecarboxylate

Participants

Reaction Steps

To a solution of [3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]acetaldehyde (D15) (97 mg) and ethyl 4-piperidinecarboxylate (234 mg) in ethanol (10.00 mL) stirred at room temperature was added sodium acetate (99 mg) and AcOH (0.069 mL). The reaction mixture was stirred at room temperature for 10 min. The residue was dissolved in dichloromethane (DCM) (10 mL), and sodium triacetoxyborohydride (154 mg) was added. Stirring continued for overnight. Water was added to quench the reaction, and DCM was removed by evaporation. The mixture was extracted by EA for 3 times. The combined organic solution was washed by brine, dried over anhydrous Na2SO4. The dried solution was filtered and concentrated to give ethyl 1-{2-[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]ethyl}-4-piperidinecarboxylate (D16) (92 mg), which was used for the next without further purification. MS (ES): C29H35ClN3O3S requires 541. found 542.3 (M+H+).

Provenance & Evidence