Trifluoroacetic acid → HCID 118293902, compound

Participants

Reaction Conditions

Reaction Steps

Selectfluor (1500.01 mg, 4.23 mmol) was added to a dry vial charged with (5S)-7-methyl-2-[4-[4-(trifluoromethyl)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]non-1-en-6-one (which may be prepared as described in Description 118) (339.99 mg, 0.9100 mmol) in anhydrous MeCN (5 mL). trifluoroacetic acid (0.04 mL, 0.5300 mmol) was added to the solution. The vial was sealed under nitrogen and was heated to 90° C. for 20 h. The reaction mixture was allowed to cool to room temperature whence it was poured into sodium hydroxide (20 mL, 10 mmol). The mixture was left to stir for 10 min and extracted with ether. The combined organic layer was dried (sodium sulfate), filtered and the filtrate was evaporated to give crude brown oil (289 mg). The crude residue was purified by silica gel chromatography (10 g SiO2) eluting with ethyl acetate in iso-hexane (10-100%), followed by purification using a ChiralPak AD-H column eluting with ethanol/n-heptane (20%:80%) to give a colourless oil, (5R)-3,3-difluoro-7-methyl-2-[4-[4-(trifluoromethyl)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]non-1-en-6-one (D120) (22 mg, 0.0537 mmol, 5.9% yield);

Provenance & Evidence