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

Temperature

-20 °C

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).

1. stirringThe resulting dark red mixture was stirred at the same temperature for 30 min
2. customThe reaction was quenched with water
3. concentrationthe mixture was concentrated
4. customThe residue was partitioned between ethyl acetate and brine
5. filtrationThe formed solid material in the bi-phase mixture was collected by filtration
6. washwashed with EtOAc and water
7. customThe obtained crude product
8. customwas recrystallized from methanol
9. customto give Example 96

ORD record

ord-f666bbdc9ca145eb93342d93c7dd2224

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08546368B2