Dimethylformamide → [6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl]-acetonitrile

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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 (0.224 g, 0.44 mmol), KCN (0.172 g, 2.65 mmol), and DMF (4 mL), and stir under nitrogen atmosphere at 100° C. After 2 hours, add ethyl acetate and water. Separate the organic phase and wash with brine. Dry the organic phase with anhydrous sodium sulfate and flash chromatograph using 0% to 20% ethyl acetate/hexanes to yield the titled compound (0.139 g, 87%) as a white foam. TLC Rf=0.46 in 4:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.31 (m, 1H), 7.24 (d, 2H, J=8.8 Hz), 6.96 (m, 3H), 6.84 (dd, 1H, J=8.4, 2.6 Hz), 3.86 (m, 6H), 3.59 (m, 1H), 3.34 (s, 1H), 3.18 (dd, 1H, J=12.3, 3.1 Hz), 2.90 (dd, 1H, J=17.2, 4.4 Hz), 2.51 (m, 2H), 1.98 (m, 1H), 1.66 (m, 2H), 1.48 (m, 2H), 1.14 (m, 3H).

Provenance & Evidence