HCID 89466854, compound → HCID 89466702, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 201A (105 mg, 0.192 mmol) in N,N-dimethylformamide (1 mL) was added copper(I) cyanide (52 mg, 0.58 mmol), and the resulting mixture was heated at 120° C. and stirred for 24 hours. The cooled mixture was partitioned between water and ethyl acetate, and the organic layer was dried over Na2SO4. The drying agent was removed by filtration, the filtrate was concentrated in vacuo, and the residue was purified on silica gel using a solvent gradient of 0-60% ethyl acetate in hexanes. The title compound was obtained as a colorless solid (70 mg, 74%). 1H NMR (300 MHz, CDCl3) δ ppm 0.88-0.99 (m, 4H), 1.77-1.91 (m, 1H), 1.93-2.06 (m, 2H), 2.35 (dd, J=10.00, 5.26 Hz, 1H), 2.39-2.61 (m, 3H), 2.81-2.96 (m, 1H), 3.03 (dd, J=8.82, 2.37 Hz, 1H), 3.68 (dd, J=10.17, 6.78 Hz, 1H), 3.89 (dd, J=10.51, 1.70 Hz, 1H), 3.96-4.08 (m, 1H), 5.23-5.39 (m, 1H), 7.90-7.98 (m, 2H), 7.99-8.06 (m, 2H), 8.30 (s, 1H); MS (ESI) m/z 494 (M+H)+.

Provenance & Evidence