Dimethyl Sulfoxide → HCID 86628524, compound

Temperature

-25 °C

A 7.18 g portion of DMSO was dissolved in 30 ml of dichloromethane, and a 10 ml dichloromethane solution of 4.0 ml oxalyl chloride was added thereto while keeping the internal temperature at −60° C. or less. After stirring for 15 minutes, a 40 ml dichloromethane solution of 6.28 g of [(3R,4S)-4-phenyl-1-(trifluoroacetyl)pyrrolidin-3-yl]methanol was added thereto while keeping the inner temperature at −60° C. and stirred for 15 minutes. A 19.3 ml portion of triethylamine was added to the reaction solution while keeping the internal temperature at −50° C. or less, and then the internal temperature was allowed to warm to −25° C. over 30 minutes or more, and this was further stirred at −25° C. for 20 minutes. Under ice-cooling, the reaction solution was added to saturated ammonium chloride aqueous solution to quench the reaction, and extracted with diethyl ether. The organic layer was washed with water and saturated brine in that order and dried with anhydrous sodium sulfate. By concentrating under a reduced pressure, (3R,4S)-4-phenyl-1-(trifluoroacetyl)pyrrolidine-3-carbaldehyde was obtained as a crude product.

1. customat −60° C. or less
2. customat −60° C.
3. stirringstirred for 15 minutes
4. customat −50° C. or less
5. stirringthis was further stirred at −25° C. for 20 minutes
6. temperatureUnder ice-cooling
7. customto quench
8. customthe reaction
9. extractionextracted with diethyl ether
10. washThe organic layer was washed with water and saturated brine in that order
11. dry with materialdried with anhydrous sodium sulfate
12. concentrationBy concentrating under a reduced pressure

ORD record

ord-e6c341d495694810acbf4bb522151511

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07585886B2