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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1925503Generated: October 28, 2026

Tetrabutylammonium Fluoride Trihydrate → 5-{(1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-8-(benzyloxy)quinolin-2(1H)-one

https://huagongshe.com/reaction/1925503

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrabutylammonium Fluoride TrihydrateHCID 11726816—
Reactant5-((1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-8-(benzyloxy)quinolin-2(1H)-oneHCID 67520893—
SolventTetrahydrofuranHCID 8028—
Product5-{(1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-8-(benzyloxy)quinolin-2(1H)-oneHCID 6752063793%

Reaction Conditions

Temperature45 °C

Reaction Steps

To a solution of Intermediate 32 (0.48 g, 0.68 mmol) in tetrahydrofuran (12 mL) was added tetrabutylammonium fluoride trihydrate (0.284 g, 1.09 mmol). The reaction mixture was stirred at 45° C. for 3.5 hours. The solvent was removed under reduced pressure and the crude was partitioned between ethyl acetate and water. The organic layer was washed several times with water and the solvent was removed under reduced pressure to give the title compound as a yellow solid (0.375 g, 88%). MS (M+): 593.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08178679B2
Source datasetuspto-grants-2012_05
ORD IDord-a23753e32f414c7b91506d663dbea864
Source noteuspto-grants-2012_05