Isopropanol → HCID 69438229, compound

Participants

Reaction Steps

To a solution of Example 86F (250 mg, 0.68 mmol), isopropanol (78 μL, 1.02 mmol) and triphenylphosphine (267 mg, 1.02 mmol) in tetrahydrofuran (5 mL) was added diethyl azodicarboxylate (175 μL, 1.02 mmol) at 25° C. The reaction was stirred for 16 hours and concentrated. The concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 30% ethyl acetate in hexanes to provide 272 mg of the title compound (84%) as a off-white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.26 (d, J=5.88 Hz, 6H) 1.82 (d, J=6.99 Hz, 3H) 4.55-4.74 (m, 1H) 5.64 (q, J=6.99 Hz, 1H) 6.83-7.05 (m, 3H) 7.18 (s, 1H) 7.38 (t, J=8.27 Hz, 1H) 7.83-7.95 (m, 4H) 7.96 (s, 1H); MS (ESI) m/z 476.1 (M+H)+.

Provenance & Evidence