2,2,6,6-Tetramethylpiperidine → HCID 136414497, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 2,2,6,6-tetramethylpiperidine (1.66 mL, 9.8 mmol) in anhydrous THF (20 mL) was added n-butyllithium (2.5 M solution in hexane, 3.92 mL, 9.8 mmol) at −20° C. The solution was stirred at −20° C. for 30 min, and a solution of Example 96A (1.0 g, 3.92 mmol) in 10 mL of anhydrous THF was added dropwise. The resulting dark red mixture was stirred at the same temperature for 30 min. The reaction was quenched with water, and the mixture was concentrated. The residue was partitioned between ethyl acetate and brine. The formed solid material in the bi-phase mixture was collected by filtration, washed with EtOAc and water. The obtained crude product was recrystallized from methanol to give Example 96. Yield: 343 mg (40%). MS (DCI): m/z 219 (M+H)+; 1H NMR (300 MHz, DMSO-d6): δ 1.71-1.79 (m, 2H), 2.33-2.37 (m, 5H), 3.20-3.25 (m, 2H), 3.65 (s, 3H), 6.04 (br s, 1H), 11.06 (br s, 1H).

Provenance & Evidence