Formic Acid → HCID 86720834, compound

Participants

Reaction Steps

4-(((R)-2-(8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl) (tert-butoxycarbonyl)amino)butyl 5-((3-((S)-phenyl(((R)-quinuclidin-3-yloxy)carbonylamino)methyl)phenoxy)methyl)furan-2-carboxylate (2.1 g, 1.990 mmol), 10% Pd/C (0.106 g, 0.099 mmol) and formic acid (0.092 mL, 2.388 mmol) were dissolved in MeOH (44.2 mL) and stirred at RT under balloon pressure of H2. After 2 hours reaction was complete and it was filtered on a pad of celite and the filtrate concentrated under reduced pressure to give a colourless viscous oil. The oil was dispersed in Et2O/AcOEt and evaporated 3 times in order to obtain a heavy white foam that was triturated in hexane/Et2O/AcOEt to give a white solid that was collected by filtration. The mother liquor was concentrated to give 0.44 g of a second crop of a whitish foam. The 2 crops were reunited to give 4-(tert-butoxycarbonyl((R)-2-(tert-butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)butyl 5-((3-((S)-phenyl(((R)-quinuclidin-3-yloxy)carbonylamino)methyl)phenoxy)-methyl)furan-2-carboxylate formate (1.95 g, 1.928 mmol, 97% yield) as white amorphous solid.

Provenance & Evidence