Methanol → HCID 68212573, compound

Participants

Reaction Conditions

Reaction Steps

Cis-2-{4-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-phenyl}-8-oxa-2-aza-spiro[4.5]decan-1-one (intermediate 19) (500 mg, 1.13 mmol) was dissolved in THF (10 mL). To this solution at rt was added TBAF (1 M in THF) (2.9 mL, 2.9 mmol, 2.5 equiv.). The reaction mixture was then heated to 60° C. (external) for 5 h. After the reaction was complete (TLC, 5% MeOH in DCM), the reaction was diluted with EtOAc (5 mL), quenched with NH4Cl (aq. saturated, 5 mL). The two layers were separated and the aq. layer was extracted with EtOAc (2×15 mL). The EtOAc solution was combined, washed with NH4Cl aq, NaHCO3 aq, and brine (10 mL each), sequentially, 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 0.375 g (100% yield) of the title compound as a white solid.

Provenance & Evidence