1-Methyl-1,4-cyclohexadiene → (R)-5-(2-Amino-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one hydrochloride

Temperature

60 °C

To a solution of (R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one (4.50 g, 10.0 mmol) in ethanol (50 mL) was added 10% palladium on charcoal (4.50 g) followed by 1-methyl-1,4-cyclohexadiene (11.0 mL, 97.9 mmol). The reaction was warmed to 60° C. and then stirred at 60° C. for 2 hours. The reaction mixture was allowed to cool and filtered through a pad of celite. The filtercake was washed with further ethanol and the filtrate was evaporated at reduced pressure. The residue was evaporated from iso-propanol (×2) and dissolved in iso-propanol (30 mL). HCl-dioxane (4 M, 50 mL, 200 mmol) was added and the reaction mixture stirred at RT for 18 hours. The resultant suspension was filtered, the filtercake washed with ether and the solid dried under vacuum in the presence of P2O5 to afford the title compound (1.65 g, 62%).

1. temperatureto cool
2. filtrationfiltered through a pad of celite
3. washThe filtercake was washed with further ethanol
4. customthe filtrate was evaporated at reduced pressure
5. customThe residue was evaporated from iso-propanol (×2)
6. dissolutiondissolved in iso-propanol (30 mL)
7. stirringthe reaction mixture stirred at RT for 18 hours
8. filtrationThe resultant suspension was filtered
9. washthe filtercake washed with ether
10. dry with materialthe solid dried under vacuum in the presence of P2O5

ORD record

ord-7560b14e50c94fc5b482526f2bbd4b60

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987299B2