benzyl[2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl)hexahydro-2,5-methanopentalene-3a(1H)-yl]carbamate → 1-[4-(1,1-Dioxidoisothiazolidin-2-yl) phenyl]tricyclo[3.3.1.03,7]nonan-3-amine

Participants

Reaction Steps

A mixture of benzyl[2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl)hexahydro-2,5-methanopentalene-3a(1H)-yl]carbamate (0.8 g, 1.7 mmol) obtained in step I, Pd/C (10%, 0.4 g) in MeOH (17 mL) was stirred at room temperature under H2 atmosphere for 2 h. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure to obtain 1-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]tricyclo[3.3.1.03,7]nonan-3-amine as an off-white solid (0.49 g) in 85% yield. m/z (M+1) 333; IR cm−1 3418, 1652, 1137, 772. 1H NMR (CDCl3) 300 MHz, δ 7.31 (d, J=8.8 Hz, 2H), 7.22 (d, J=8.8 Hz, 2H), 3.78 (t, J=6.6 Hz, 2H), 3.43 (t, J=7.4 Hz, 2H), 2.58-2.47 (m, 3H), 2.40-2.34 (m, 1H), 2.27-2.11 (m, 2H), 2.10-1.95 (m, 4H), 1.93-1.70 (m, 4H).

Provenance & Evidence