Chloroform → HCID 21309650, compound

Participants

Reaction Steps

The compound from step 13a (805 mg, 2.68 mmol) was treated in a similar fashion as that described under Example 7d. The crude was subject to flash chromatography on silica gel with 10% MeOH in CHCl3 to 0.5% NH4OH in 10% MeOH in CHCl3 used as the elutant to give 352 mg of a yellow oil (66% yield). MS (CI) m/e 200 (M+H)+. The amine deprotected material (330 mg, 1.66 mmol) was then subjected to reductive amination conditions previously described in Example 8. The crude product was purified by flash chromatography on silica gel using 2% MeOH in CHCl3 to 5% MeOH in CHCl3 as the elutant to give 125 mg of a clear oil (35% yield). MS (CI) m/e 214 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 7.36 (d, J=9.2 Hz, 1H), 7.02 (d, J=9.2 Hz, 1H, 4.54 (dd, J=11.6 Hz, 3.8 Hz, 1H), 4.47 (dd, J=11.6 Hz, 5.7 Hz, 1H, 3.48-3.39 (m, 2H), 2.89-2.81 (m, 1H), 2.38 (s, 3H), 2.17-2.03 (m, 2H).

Provenance & Evidence