HCID 71544157, compound → HCID 86680451, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from Example 64A (30 mg, 0.055 mmol) in N,N-dimethylformamide (0.3 mL) was added copper(I) cyanide (10 mg, 0.11 mmol), and the resulting mixture was stirred at 130° C. for 16 hours. The cooled mixture was partitioned between water and ethyl acetate (3×), and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-60% ethyl acetate in hexanes to give the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 0.87-1.00 (m, 4H), 1.74-1.90 (m, 1H), 1.91-2.07 (m, 2H), 2.19 (t, J=10.34 Hz, 1H), 2.34 (dd, J=10.17, 5.09 Hz, 1H), 2.39-2.63 (m, 3H), 2.98-3.10 (m, 1H), 3.66 (dd, J=10.17, 6.78 Hz, 1H), 3.80 (dd, J=10.17, 1.70 Hz, 1H), 3.88-3.99 (m, 1H), 5.24-5.36 (m, 1H), 7.92 (d, J=1.36 Hz, 1H), 8.03 (d, J=1.36 Hz, 1H), 8.11-8.14 (m, J=1.02 Hz, 1H), 8.17-8.26 (m, J=4.07, 1.02 Hz, 2H); MS (ESI) m/z 494.0 (M+H)+.

Provenance & Evidence