2,2,6,6-Tetramethylpiperidine → HCID 46941343, compound

Temperature

-78 °C

To a solution of 2,2,6,6-tetramethylpiperidine (0.99 g, 7.02 mmol) in THF (25 ml) was added n-BuLi (2.80 ml, 2.5 M hexane solution, 7.02 mmol) at −10° C. After stirring for 10 min, this solution was cooled to −78° C., tris(1-methylethyl)borate (1.58 g, 8.4 mmol) was added, and the mixture was stirred for 5 min. To this solution was added a solution of 2-(trifluoromethyl)benzonitrile (1.00 g, 5.85 mmol) in THF (10 ml), and the mixture was stirred at −78° C. for 2 hr. The reaction solution was allowed to warm to room temperature, the reaction was quenched with acetic acid, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, the precipitated solid was filtered off, and the filtrate was concentrated to give the title compound (3.14 g) as a mixture. This was used for the next reaction without performing further purification and identification.

1. stirringthe mixture was stirred for 5 min
2. stirringthe mixture was stirred at −78° C. for 2 hr
3. temperatureto warm to room temperature
4. customthe reaction was quenched with acetic acid
5. customthe solvent was evaporated under reduced pressure
6. additionEthyl acetate was added to the residue
7. filtrationthe precipitated solid was filtered off
8. concentrationthe filtrate was concentrated

ORD record

ord-fd33608f16a246d0a773c264f3a3cd59

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08338622B2