Acetic Acid → HCID 56658872, compound

Participants

Reaction Steps

To a solution of 9-[(4-chlorophenyl)sulfonyl]-2-(hydroxymethylidene)-7-(3-methyl-1,2,4-oxadiazol-5-yl)-9-azabicyclo[3.3.1]nonan-3-one (53) (0.38 g, 0.902 mmol) in EtOH (5 mL) was added glacial acetic acid (0.1 mL) followed by hydrazine monohydrate (0.44 mL, 9.02 mmol). The reaction mixture was stirred at room temperature for 2 h and then at 50° C. for a further 2 h. The resulting solution was diluted with EtOAc and washed with H2O. The organic phase was dried (Na2SO4), filtered, concentrated and purified by silica gel column chromatography (eluant hexane/EtOAc, 9/1 to 2/8) and preparative HPLC to give 10-[(4-chlorophenyl)sulfonyl]-6-(3-methyl-1,2,4-oxadiazol-5-yl)-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazole (54). MS (ESI) 420.1 (M+H). 1H NMR (300 MHz, CDCl3) δ 7.67 (d, J=8.8 Hz, 2H), 7.52 (s, 1H), 7.39 (d, J=8.8 Hz, 2H), 5.43 (bs, 1H), 4.66 (bs, 1H), 3.06 (m, 1H), 2.72 (d, J=17.6 Hz, 1H), 2.34 (s, 3H), 2.32-2.09 (m, 4H).

Provenance & Evidence