Methyl iodide → HCID 11675645, compound

Participants

Reaction Conditions

Reaction Steps

Crude 18-3 (100 mg, 0.2 mmol) was dissolved in anhydrous DMF (3 mL) and cooled to 0° C. under N2. NaH (28 mg, 1.17 mmol) was added neat and the reaction was stirred 30 minutes at 0° C. Following cessation of H2 evolution, MeI (0.15 mL, 2.4 mmol) was added and the reaction was stirred 12 hours at 25° C. Upon completion, the reaction was diluted with EtOAc (10 mL), and the organic layer was washed successively with 5% NH4Cl (1×10 mL), H2O (3×5 mL) and brine (1×10 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The crude oil was dissolved in anhydrous CH2Cl2 (10 mL). The resulting solution was treated with trifluoroacetic acid (5 mL) and stirred 1 hour at 25° C. Upon completion, the reaction was concentrated and directly subjected to reverse-phase column chromatography to provide 18-4: 1H NMR (300 MHz, CD3OD) δ 7.33 (m, 4H), 7.25 (m, 2H), 7.17 (m, 1H), 7.08 (m, 1H), 6.41 (s, 1H), 6.00 (t, J=2.7 Hz, 1H), 5.07 (ddd, J=14.0, 5.6, 1.7 Hz, 1H), 4.55 (d, J=14.0 Hz, 1H), 3.82 (m, 1H), 3.40 (m, 2H), 3.03 (dt, J=12.5, 3.9 Hz, 1H), 2.88 (s, 3H), 2.81 (dt, J=13.1, 2.9 Hz, 1H), 1.90 (m, 4H); LRMS m/z (M+H) 398.0 found, 398.2 required.

Provenance & Evidence