Pyrrolidine → 1-[6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl]-pyrrolidine

Participants

Reaction Steps

Combine toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl ester (0.087 g, 0.175 mmol), pyrrolidine (0.09 mL, 1.05 mmol), and benzene (5 mL), and reflux under nitrogen atmosphere. After 18 hours, concentrate reaction under vacuum then add ethyl acetate and wash with sodium bicarbonate solution (aq). Separate the organic phase and wash with brine. Dry the organic phase with anhydrous sodium sulfate and flash chromatograph using 2% to 4% (2M NH3 methanol)/methylene chloride to yield the titled compound (0.060 g, 86%) as a white solid. TLC Rf=0.25 in 4% 2M NH3 methanol:DCM. 1H NMR (CDCl3): 7.95 (d, 1H, J=8.4 Hz), 7.24 (d, 2H, J=8.4 Hz), 6.91 (m, 3H), 6.79 (dd, 1H, J=8.6, 2.4 Hz), 3.85 (s, 6H), 3.34 (t, 1H, J=9.2 Hz), 3.22 (s, 1H), 3.07 (dd, 1H, J=11.7, 3.3 Hz), 2.74 (dd, 1H, J=12.3, 7.5 Hz), 2.42 (m, 4H), 2.20 (m, 2H), 1.89 (m, 1H), 1.66 (m, 6H), 1.43 (m, 2H), 1.17 (m, 3H); MS m/z 406 (M+1).

Provenance & Evidence