Acetic Acid → 1-(1,1-Dioxido iso thiazolidin-2-yl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid

Participants

Reaction Steps

To a stirred mixture of NaOH (2.1 g, 53.0 mmol), H2O (14 mL), and 1,4 dioxane (4 mL) at ice bath temperature was added Br2 (1.0 mL, 19.8 mmol) and the mixture was stirred for 5 minutes. Thus formed hypobromite solution was added drop-wise to a stirred solution of the compound obtained in step I (1.0 g, 3.53 mmol) in 1,4-dioxane (7 mL) at 10° C. The temperature of the reaction was gradually brought to room temperature and the reaction was stirred for 1 h, then it was cooled to ice bath temperature and quenched by adding AcOH (3.9 mL, 65.7 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-dioxido iso thiazolidin-2-yl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid as a viscous liquid (0.9 g) in 90% yield. m/z (M+1) 286; 1H NMR (CDCl3) 300 MHz δ 3.37 (t, J=6.6 Hz, 2H), 3.16 (t, J=7.8 Hz, 2H), 2.84-2.76 (m, 1H), 2.52-2.41 (m, 2H), 2.38-2.26 (m, 2H), 2.25-1.98 (m, 6H), 1.85-1.72 (m, 2H), 1.61 (dd, J=2.2, 11.3 Hz, 1H).

Provenance & Evidence