Sulfuric Acid → 1-(1,1-Dioxidoisothiazolidin-2-yl)tricyclo[3.3.1.03,7]nonan-3-amine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the acid obtained in step II (0.29 g, 1.0 mmol) in CHCl3 (5 mL) at room temperature was added conc. H2SO4 (0.53 mL, 10 mmol) followed by the addition NaN3 (0.2 g, 3.0 mmol) in portions over a period of 30 min; while maintaining the temperature below 40° C. The reaction mixture was warmed to 45° C. and stirred for 2 h. The reaction mixture was cooled to ice bath temperature, diluted with water and extracted with EtOAc. The aqueous layer was basified by adding a 50% NaOH solution and extracted with CHCl3. 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)tricyclo[3.3.1.03,7]nonan-3-amine as a viscous liquid (0.17 g) in 66% yield. m/z (M+1) 257; 1H NMR (CDCl3) 300 MHz δ 3.36 (t, J=6.6 Hz, 2H), 3.15 (t, J=7.5 Hz, 2H), 2.40-2.24 (m, 4H), 2.18 (dd, J=3.0, 10.4 Hz, 1H), 2.13-1.83 (m, 6H), 1.76 (dd, (J=2.4, 10.8 Hz, 1H), 1.65-1.58 (m, 1H), 1.48 (dd, J=2.4, 10.8 Hz, 1H).

Provenance & Evidence