Dimethyl Sulfoxide → tert-Butyl 4-formylpiperidine-1-carboxylate

Temperature

-78 °C

Dichloromethane solution of DMSO (2.4 mL, 33.4 mmol) was added to dichloromethane solution of oxalyl chloride (1.5 mL, 16.7 mmol) at −76° C. for 30 minutes. After stirring for 30 minutes at −78° C., dichloromethane solution (15 mL) of 4-(hydroxymethyl)piperidine-1-carboxilic acid tert-butyl ester (3.00 g, 13.9 mmol) was added at −76° C. for 30 minutes. After stirring for 30 minutes at −76° C., triethylamine (9.7 mL) was added at −76° C. for 10 minutes. The mixture was stirred at −76° C. for 15 minutes and was stirred for 45 minutes after increasing the temperature to room temperature. The reaction was terminated by adding water. The reaction mixture was extracted with dichloromethane three times. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1) to obtain compound P33 (2.41 g, 11.3 mmol, 81%).

1. stirringAfter stirring for 30 minutes at −76° C.
2. stirringThe mixture was stirred at −76° C. for 15 minutes
3. stirringwas stirred for 45 minutes
4. temperatureafter increasing the temperature to room temperature
5. customThe reaction was terminated
6. additionby adding water
7. extractionThe reaction mixture was extracted with dichloromethane three times
8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1)
11. customto obtain compound P33 (2.41 g, 11.3 mmol, 81%)

ORD record

ord-564b8fe95d0946299ce460822bb7ea92

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507484B2