Trifluoroacetic acid → HCID 58513737, compound

Temperature

50 °C

To an ambient solution of tert-butyl 3-(thiazol-2-yl)-3-(2-(tosyloxy)ethoxy)pyrrolidine-1-carboxylate (2.3 g, 4.91 mmol) in dichloromethane (24.54 ml) was added trifluoroacetic acid (0.378 mL, 4.91 mmol). The reaction was stirred for 2 hours and was then concentrated under reduced pressure. The residue was dissolved in dichloromethane (10 mL), and the solution was added slowly to an ambient mixture of potassium carbonate (6.78 g, 49.1 mmol) in dichloromethane (50 mL). The mixture was heated to 50° C. for 1 hour and then cooled to room temperature. The reaction was diluted with water (100 mL). The layers were separated, and the aqueous layer was extracted with additional dichloromethane (2×). The combined organics were dried with anhydrous sodium sulfate, filtered and dried under reduced pressure, to give the title compound, which was used without further purification. MS ESI(+) m/z 197.1 [M+H]+.

1. concentrationwas then concentrated under reduced pressure
2. dissolutionThe residue was dissolved in dichloromethane (10 mL)
3. temperaturecooled to room temperature
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with additional dichloromethane (2×)
6. dry with materialThe combined organics were dried with anhydrous sodium sulfate
7. filtrationfiltered
8. customdried under reduced pressure

ORD record

ord-c2288f56f1f24267b5be2f80401f595c

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691810B2