Sulfuric Acid → 1-Methoxytricyclo[3.3.1.03,7]nonan-3-amine

Participants

Reaction Steps

To the suspension of 1-methoxytricyclo[3.3.1.03,7]nonane-3-carboxylic acid obtained from step IV (0.39 g, 2.0 mmol) in CHCl3 (10 mL) was added conc. H2SO4 (1.0 mL, 20 mmol). Solid NaN3 (0.39 g, 6.0 mmol) was added in portions by keeping the reaction temperature below 40° C. After stirring at room temperature for 2 hrs, the reaction mixture was cooled to ice bath temperature, diluted with water and extracted with EtOAc. The aqueous layer was basified by adding 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-methoxytricyclo[3.3.1.03,7]nonan-3-amine (0.23 g) in 69% yield. m/z (M+1) 168; 1H NMR (CDCl3) 300 MHz δ 3.27 (s, 3H), 2.40-2.34 (m, 1H), 2.16-2.08 (m, 1H), 1.97 (ddd, J=2.0, 6.8, 8.7 Hz, 1H), 1.92-1.53 (m, 7H), 1.51-1.38 (m, 2H).

Provenance & Evidence