Dimethyl Sulfoxide → 1-[2,4-Bis(trifluoromethyl)benzyl]-2-oxopiperidine-4-carbaldehyde

Temperature

-78 °C

To a solution of oxalyl chloride (4.5 mL) in dichloromethane (80 mL) was added a solution of dimethyl sulfoxide (7.3 mL) in dichloromethane (50 mL) under cooling to −78° C. The reaction mixture was stirred for 30 min under cooling to −78° C., and to the reaction mixture was added dropwise a solution of 1-[2,4-bis(trifluoromethyl)benzyl]-4-(hydroxymethyl)piperidin-2-one (10 g) in dichloromethane (50 mL). The reaction mixture was stirred for 40 min under cooling to −78° C., triethylamine (19.7 mL) was added, and the mixture was further stirred at room temperature for 30 min. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with dichloromethane. The extract was washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (3.7 g).

1. temperatureunder cooling to −78° C.
2. stirringThe reaction mixture was stirred for 40 min
3. temperatureunder cooling to −78° C.
4. stirringthe mixture was further stirred at room temperature for 30 min
5. extractionthe mixture was extracted with dichloromethane
6. washThe extract was washed with saturated brine
7. dry with materialdried over sodium sulfate
8. customthe solvent was evaporated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

ORD record

ord-94bb054148b7426c864346f923180f6f

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772277B2