Hydrochloric Acid → HCID 59281217, compound

[(2R,4R,5S)-5-Amino-2-benzyloxymethyl-5-(5-bromo-2-fluorophenyl)tetrahydropyran-4-yl]methanol (2.22 g) was dissolved in dichloromethane (30 ml), and benzoyl isothiocyanate (776 μl) was added. The mixture was stirred at room temperature for five hours, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain an intermediate. The resulting intermediate was dissolved in methanol (50 ml), and concentrated hydrochloric acid (2 ml) was added. The mixture was heated under reflux for six hours and then cooled to room temperature. The solvent was evaporated under reduced pressure. Methanol (30 ml) and DBU (2 ml) were added to the residue, followed by heating under reflux for three hours. The reaction solution was cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was purified by NH-silica gel column chromatography to obtain the title compound (2.30 g).

1. customthe solvent was evaporated under reduced pressure
2. customThe residue was purified by silica gel column chromatography
3. customto obtain an intermediate
4. temperatureThe mixture was heated
5. temperatureunder reflux for six hours
6. temperaturecooled to room temperature
7. customThe solvent was evaporated under reduced pressure
8. additionMethanol (30 ml) and DBU (2 ml) were added to the residue
9. temperatureby heating
10. temperatureunder reflux for three hours
11. temperatureThe reaction solution was cooled to room temperature
12. customthe solvent was evaporated under reduced pressure
13. customThe residue was purified by NH-silica gel column chromatography

ORD record

ord-f4597f2fcba24b7cb90bf2551bec114e

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08198269B2