Acetic Acid → 1-[(1,1-Dioxidoisothiazolidin-2-yl)methyl]tricyclo[3.3.1.03,7]nonane-3-carboxylicacid

Participants

Reaction Steps

To a stirred mixture of NaOH (1.2 g, 27.8 mmol), H2O (8 mL), and 1,4 dioxane (1 mL) at ice bath temperature was added Br2 (0.56 mL, 10.4 mmol) and the mixture was stirred for 15 minutes. The resulting hypobromite solution was added drop-wise to a stirred solution of the compound obtained in step II (0.55 g, 1.85 mmol) in 1,4-dioxane (3 mL) at ice bath temperature. The reaction mixture was gradually warmed to room temperature and after stirring for 1 h; it was cooled to ice bath temperature and quenched by adding AcOH (1.7 mL, 27.8 mmol). The 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-[(1,1-dioxidoisothiazolidin-2-yl)methyl]tricyclo[3.3.1.03,7]nonane-3-carboxylicacid (0.39 g) in 70% yield. m/z (M−1) 298; 1H NMR (CDCl3) 300 MHz δ 3.32 (t, J=6.8 Hz, 2H), 3.10 (t, J=7.4 Hz, 2H), 2.95 (s, 2H), 2.80-2.73 (m, 1H), 2.43-2.41 (m, 1H), 2.40-2.29 (m, 2H), 2.10-2.0 (m, 2H), 1.82-1.72 (m, 3H), 1.67-1.54 (m, 4H), 1.46 (dd, J=3.2, 11.0 Hz, 1H).

Provenance & Evidence