Hydrochloric Acid → HCID 57437812, compound

Temperature

130 °C

A mixture of 4-(chloromethyl)-6,7-dihydro-4H-thieno[3,2-c]pyran (1 g, 5.305 mmol, 1 eq), pyrrolidine (11.3 g, 159.1 mmol, 30 eq) and NaI (50 mg) in DMF (50 mL) in a sealed tube was stirred at 130° C. for 6 hr. The reaction mixture was cooled and poured into H2O and the pH was adjusted to ˜2 with 2N HCl. The resulting solution was washed with EtOAc. The aqueous layer was then adjusted to pH 9-10 and extracted with EtOAc. The EtOAc layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The resulting crude product was purified by preparative HPLC. After removal of organic volatiles of the collected HPLC fractions, the pH of remaining aqueous phase was adjusted to ˜8 with saturated Na2CO3 solution. The aqueous solution was extracted with EtOAc (3 times). The combined EtOAc extract was washed with brine, dried with Na2SO4, and concentrated to give the desired product.

1. temperatureThe reaction mixture was cooled
2. washThe resulting solution was washed with EtOAc
3. extractionextracted with EtOAc
4. washThe EtOAc layers were washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe resulting crude product was purified by preparative HPLC
9. customAfter removal of organic volatiles of the collected HPLC fractions
10. extractionThe aqueous solution was extracted with EtOAc (3 times)
11. extractionThe combined EtOAc extract
12. washwas washed with brine
13. dry with materialdried with Na2SO4
14. concentrationconcentrated

ORD record

ord-d3b583289fa24ac2ab04068ffb046d28

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710245B2