Hydrochloric Acid → HCID 57448164, compound

To 1D (1.50 g, 4.67 mmol) in MeOH (23 mL) and water (5 mL) was added potassium carbonate (3.20 g, 23.4 mmol) and the reaction was refluxed for 45 min. After cooling to rt, the mixture was filtered and the filtrate was concentrated. The resulting residue was dissolved in ethyl acetate and washed with water and brine. The aqueous layer was back-extracted with ethyl acetate (5×). The combined organic layers were dried (MgSO4), filtered and concentrated to provide a yellow oil. The oil was dissolved in THF and 4N HCl in 1,4-dioxane (2.2 mL) was added. The resulting white solid was filtered to provide 1E (1.00 g). 1H NMR (400 MHz, CD3OD) δ ppm 1.03-1.21 (m, 2H), 1.30 (ddd, J=7.14, 4.50, 4.17 Hz, 2H), 2.80 (s, 3H), 2.84-3.03 (m, 1H), 2.86-3.05 (m, 1H), 4.41-4.65 (m, 2H), 7.59-7.93 (m, 3H), 8.06 (d, J=7.91 Hz, 1H). LC-MS: 226.10 (M+H)+.

1. temperaturethe reaction was refluxed for 45 min
2. filtrationthe mixture was filtered
3. concentrationthe filtrate was concentrated
4. dissolutionThe resulting residue was dissolved in ethyl acetate
5. washwashed with water and brine
6. extractionThe aqueous layer was back-extracted with ethyl acetate (5×)
7. dry with materialThe combined organic layers were dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customto provide a yellow oil
11. filtrationThe resulting white solid was filtered

ORD record

ord-8b56409d3b6d42d6bbcb34ecf1133bae

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08044242B2