Acetic Acid → 1-(1H-1,2,4-triazol-1-ylmethyl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid

Participants

Reaction Steps

To a stirred solution of NaOH (1.75 g, 43.8 mmol), H2O (14.6 mL) and 1,4 dioxane (2 mL) at ice bath temperature was added Br2 (0.8 mL, 16.4 mmol) and the mixture was stirred for 5 minutes. The resulting hypobromite solution was added drop-wise to a stirred solution of 1-[1-(1H-1,2,4-triazol-1-ylmethyl)tricyclo[3.3.1.03,7]non-3-yl]ethanone (0.7 g, 2.92 mmol) in 1,4-dioxane (4 mL) at ice bath temperature. The reaction mixture was gradually warmed to room temperature and stirred for 1 h. Then it was cooled to ice bath temperature and quenched by adding AcOH (3.9 mL, 65.7 mmol). The crude reaction mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 1-(1H-1,2,4-triazol-1-ylmethyl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid (0.54 g) in 75% yield as an off-white solid. M.R: 230-235° C. m/z (M+1) 248. IR cm−1 3436, 3102, 2924, 2511, 1937, 1689, 1523, 1308, 1137, 979, 732. 1H NMR (CD3OD) 300 MHz δ 8.43 (s, 1H), 7.9 (s, 1H), 4.17 (s, 2H), 2.70-2.62 (m, 1H), 2.40-2.33 (m, 1H), 2.06-1.95 (m, 2H), 1.84-1.1.43 (m, 8H).

Provenance & Evidence