Cesium fluoride → tert-butyl 4a-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo-[4,5-b]pyridin-5-yl]-4,4-difluorooctahydro-2H-cyclopropa[3,4]cyclopenta[1,2-c]pyrrole-2-carboxylate

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Reaction Conditions

Reaction Steps

tert-Butyl 5-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-3,3a,4,6a-tetrahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (8-3, 73 mg, 0.17 mmol, 1.0 equiv) and cesium fluoride (2.6 mg, 0.02 mmol, 0.1 equiv) were added to anhydrous toluene (428 μL) and the resulting mixture was placed in a 100° C. bath. A solution of trimethylsilyl difluoro(fluorosulfonyl)acetate (30-1, 176 mg, 0.70 mmol, 4.1 equiv) in anhydrous toluene (1.3 mL) was then added dropwise via syringe pump over a period of 8 h. After stirring at 100° C. for an additional 6 h, the contents were filtered through Celite and purified by reverse-phase HPLC (40-100% 0.1% TFA in H2O:CH3CN) to give 30-2 as a colorless semi-solid. MS m/z (M+H): calculated=509.1276; observed=509.1278.

Provenance & Evidence