1-Methyl-1,4-cyclohexadiene → (R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-one

Participants

Reaction Steps

To an ice-cooled suspension of palladium on activated carbon (4.50 g, 10% w/w) and (R)-5-(2-azido-1-(tert-butyldimethylsilyloxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one (4.50 g, 10.0 mmol) in ethanol (50 mL) was added drop-wise 1-methyl-1,4-cyclohexadiene (11.0 mL, 97.9 mmol). The coolant was removed, and the suspension stirred at ambient temperature for 10 minutes and then heated to 50° C. for one hour. The reaction mixture was allowed to cool and the suspension filtered through celite. The filter-cake was washed with further ethanol, and the combined filtrates concentrated under reduced pressure. The residue was triturated with acetonitrile to afford the title compound (3.03 g, 90%).

Provenance & Evidence