Sulfuric Acid → 1-(3-Aminotricyclo[3.3.1.03,7]non-1-yl)pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the acid obtained in step II (0.5 g, 2.0 mmol) in CHCl3 (21 mL) at room temperature was added conc. H2SO4 (1.0 mL, 20 mmol) followed by NaN3 (0.39 g, 6.0 mmol) in portions over a period of 30 min., so that the temperature of the reaction did not rise above 40° C. The reaction was warmed to 45° C. and stirred for 2 h, then 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-(3-aminotricyclo[3.3.1.03,7]non-1-yl) pyrrolidin-2-one as an off-white solid (0.25 g) in 74% yield. m/z (M+1) 221; 1H NMR (CDCl3) 300 MHz δ 3.41 (t, J=7.0 Hz, 2H), 2.46 (dd, J=2.4, 10.3 Hz, 1H), 2.38-2.28 (m, 1H), 2.30 (t, J=8.3 Hz, 2H), 2.16-1.82 (m, 9H), 1.78 (dd J=2.6, 10.8 Hz, 1H), 1.66-1.58 (m, 1H), 1.51 (dd, J=2.5, 10.8 Hz, 1H).

Provenance & Evidence