Methanol → 2-[2-Fluoro-4-(4-hydroxy-cyclohexyl)-phenyl]-1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

2-{4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-2-fluoro-phenyl}-1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester (720 mg, 1.29 mmol) was dissolved in THF (10 mL). To this solution at rt was added TBAF (1M in THF) (2 mL, 2 mmol, 1.5 equiv.). The reaction mixture was then heated to 60° C. (bath set) for 5 h. The reaction was complete (TLC, 5% MeOH in DCM). The reaction was diluted with EtOAc (5 mL), quenched with NaHCO3 (saturated aqueous solution, 5 mL). The two layers were separated and the aq. layer was extracted with EtOAc (15 mL×2). The EtOAc solution was combined, washed with brine (10 mL), and dried over K2CO3, filtered, and concentrated. The crude product was purified on a silica gel column eluted with 5% MeOH in DCM to afford 0.53 g (93% yield) of the title compound as a white solid.

Provenance & Evidence