Ammonium Acetate → HCID 57816628, compound

Temperature

130 °C

A mixture of (2S)-tert-butyl 2-(7-bromo-4-oxochroman-3-ylcarbamoyl)pyrrolidine-1-carboxylate (3.23 g, 7.35 mmol) and ammonium acetate (5.6 g, 73.5 mmol) in xylenes (40 mL) was heated at 130° C. for 2 hours. The reaction was cooled to room temperature. The xylenes were removed under reduced pressure and the residue was diluted with dichloromethane (100 mL). Saturated sodium bicarbonate (200 mL) was added slowly with stirring until gas evolution had subsided. The phases were separated and the aqueous phase was extracted with dichloromethane (50 mL). The combined organic phases were washed with brine (50 mL) and dried over sodium sulfate. The mixture was filtered and the solvent was removed under reduced pressure. The residue was subjected to flash chromatography with eluant of (10% methanol in ethylacetate) and hexane. The product containing fractions were combined and the solvent was removed under reduced pressure to provide (S)-tert-butyl 2-(7-bromo-3,4-dihydrochromeno[4,3-d]imidazol-2-yl)pyrrolidine-1-carboxylate (1.77 g, 4.21 mmol, 57%).

1. temperatureThe reaction was cooled to room temperature
2. customThe xylenes were removed under reduced pressure
3. additionthe residue was diluted with dichloromethane (100 mL)
4. additionSaturated sodium bicarbonate (200 mL) was added slowly
5. customThe phases were separated
6. extractionthe aqueous phase was extracted with dichloromethane (50 mL)
7. washThe combined organic phases were washed with brine (50 mL)
8. dry with materialdried over sodium sulfate
9. filtrationThe mixture was filtered
10. customthe solvent was removed under reduced pressure
11. additionThe product containing fractions
12. customthe solvent was removed under reduced pressure

ORD record

ord-e2642b64680a48198aa3ded39199480b

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156823B2