Sodium Carbonate → HCID 46861600, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (5-{3-[5-(trifluoromethoxy)-3,4-dihydro-1′H-spiro[chromene-2,4′-piperidin]-1′-yl]-4,5-dihydroisoxazol-5-yl}-2H-tetrazol-2-yl)acetate A suspension of dried Na2CO3 (694 mg, 6.55 mmol) in anhydrous t-BuOH was added 5-(trifluoromethoxy)-3,4-dihydrospiro[chromene-2,4′-piperidinium]chloride (848 mg, 2.62 mmol) (Intermediate 8) and tert-butyl[5-(3-bromo-4,5-dihydroisoxazol-5-yl)-2H-tetrazol-2-yl]acetate (725 mg, 2.183 mmol) (Intermediate 7). The mixture was directly heated to 115° C. for 24 h. The reaction mixture was diluted with MTBE, poured into aq. NH4Cl and extracted with EtOAc. The organic layer was washed with water and brine. The aqueous phases were back extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on SiO2 (50 g, gradient from 0 to 70% EtOAc/hexanes) to afford the title compound as a white solid. LC-MS: m/z=539.1 (MH+).

Provenance & Evidence