Iodine → HCID 68772367, compound

To a solution of dihydrofuran-3(2H)-one (0.5 g, 6.0 mmol, Small Molecules Inc.) in acetonitrile (10 mL) were added molecular sieves (0.5 g) and butan-1-amine (0.4 g, 5.5 mmol, Aldrich). The reaction mixture was stirred at room temperature overnight and then filtered. To the filtrate was added potassium thiocyanate (0.7 g, 7.3 mmol, Aldrich). The temperature was adjusted to 50° C. and the mixture was stirred until the solids were dissolved. Then, iodine (2.8 g, 10.9 mmol, EMD Chemicals) was added to the mixture and stirred at 50° C. overnight. The reaction mixture was cooled, concentrated and dissolved in EtOAc (15 mL). The solution was washed with Na-meta-bisulfite 20% (15 mL) by mixing the layers for 30 minutes. The organic layer was washed twice with 1N HCl (15 mL). The aqueous layers (metabisulfite and HCl) were combined and the pH was adjusted to pH ˜9 by adding NH4OH. The product was extracted with EtOAc (4×20 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated to obtain the crude product (0.22 g) of the title compound. MS (ESI+) m/z 199 (M+H)+.

1. filtrationfiltered
2. customwas adjusted to 50° C.
3. stirringthe mixture was stirred until the solids
4. dissolutionwere dissolved
5. stirringstirred at 50° C. overnight
6. temperatureThe reaction mixture was cooled
7. concentrationconcentrated
8. dissolutiondissolved in EtOAc (15 mL)
9. washThe solution was washed with Na-meta-bisulfite 20% (15 mL)
10. additionby mixing the layers for 30 minutes
11. washThe organic layer was washed twice with 1N HCl (15 mL)
12. additionby adding NH4OH
13. extractionThe product was extracted with EtOAc (4×20 mL)
14. dry with materialThe combined organic extracts were dried (Na2SO4)
15. filtrationfiltered
16. concentrationconcentrated

ORD record

ord-180b65222ca44fa8a28cb8a7916dee97

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735434B2