HCID 86619855, compound → HCID 16119582, compound

Participants

Reaction Steps

Crude intermediate 16, 3-(3-fluoro-4-((pyrrolidin-1-yl)methyl)phenyl)-N-isobutylcyclobut-2-enecarboxamide prepared above was dissolved in EtOH (100 mL) and added to a hydrogenation bottle containing 10% palladium on carbon slurried in EtOH (˜5 mL). The mixture was shaken at room temperature under 45 psi of hydrogen for 2 h, filtered through diatomaceous earth with an EtOH rinse and concentrated to yield an orange oil. This was dissolved in EtOAc (150 mL) and washed with aqueous K2CO3 and brine, dried over MgSO4 and concentrated to afford 3.29 g of waxy orange solid. Flash chromatography on a 2.5″×4″ silica gel column eluting with 1000 mL EtOAc and 500 mL 10% MeOH/EtOAc afforded 1.90 g (54%) of the title compound as a yellow tinged solid: Rf=0.26 (20% MeOH/EtOAc).

Provenance & Evidence