N-[(1S)-2-(benzyloxy)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethyl]-3-nitroquinolin-4-amine → N4-[(1S)-2-(benzyloxy)-1-({[tert-butyl(dimethyl)silyl]oxy]methyl)ethyl}quinoline-3,4-diamine

Participants

Reaction Steps

N-[(1S)-2-(Benzyloxy)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethyl]-3-nitroquinolin-4-amine (1.81 g, 3.88 mmol) was dissolved in 30 mL of acetonitrile and the solution was placed in a pressure bottle. Platinum on carbon (5%, 180 mg) was then added and the reaction mixture was shaken under H2 at 50 PSI (3.4×105 Pa). After 5.5 hours, the reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with acetonitrile and the combined filtrates were concentrated under reduced pressure to give 1.66 g of N4-[(1S)-2-(benzyloxy)-1-({[tert-butyl(dimethyl)silyl]oxy]methyl)ethyl}quinoline-3,4-diamine as an orange solid.

Provenance & Evidence