Dimethyl Sulfoxide → HCID 67065856, Verbindung

Temperatur

-60 °C

To a stirred solution of anhydrous dichloromethane (35.0 mL) in a 3-necked flask with a thermometer, oxalyl chloride (1.5 mL) was added and the resulting solution was cooled to −60° C. A solution of dimethyl sulfoxide (2.6 mL) in dichloromethane (7.5 mL) was added over a period of 10 min, and then (3R)-1-tritylpyrrolidin-3-ol (5.0 g) in dichloromethane (15.0 mL) was added over a period of 10 min. The resulting solution was stirred at −60° C. for 15 min., then triethylamine (10.6 mL) was added over a period of 5 min. A white precipitate was formed. After 5 min, the cooling bath was removed and the mixture was allowed to warm to room temperature. Water (45 mL) was added. The mixture was stirred for an additional 30 min and then extracted with dichloromethane. The organic phase was washed with 5% aqueous citric acid solution, dried over anhydrous sodium sulfate, filtered and concentrated to yield the title compound. LC-MS=243.1 (M+1).

1. customA white precipitate was formed
2. waitAfter 5 min
3. customthe cooling bath was removed
4. temperatureto warm to room temperature
5. additionWater (45 mL) was added
6. stirringThe mixture was stirred for an additional 30 min
7. extractionextracted with dichloromethane
8. washThe organic phase was washed with 5% aqueous citric acid solution
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated

ORD-Eintrag

ord-668be6e024d84ac9bbdca8fb9eb0f8f3

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08653059B2