Methyl iodide → HCID 86653599, compound

Participants

Reaction Steps

A solution of methyl (4RS,6RS)-6-(4-chloro-3-(trifluoromethyl)phenyl)-4-(hydroxymethyl)-6-methylcyclohex-1-enecarboxylate (Example 7, Step 9; 32.2 mg, 0.089 mmol) in DMF (0.25 mL) was diluted with methyl iodide (0.75 mL, 11.99 mmol) and treated with silver oxide (103 mg, 0.444 mmol). The resulting suspension was protected from ambient light and stirred at rt for 41.5 h. After this time, the mixture was diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by column chromatography on silica gel, eluting with 10-30% ethyl acetate-hexanes, to provide methyl (4RS,6RS)-6-(4-chloro-3-(trifluoromethyl)phenyl)-4-(methoxymethyl)-6-methylcyclohex-1-enecarboxylate as a colorless gum (20 mg, 60%). Mass spectrum m/z 394.1 (M+NH4+). 1H NMR (400 MHz, CDCl3) δ 7.55 (d, J=2.2 Hz, 1 H), 7.38 (d, J=8.4 Hz, 1 H), 7.31 (dd, J=8.4, 2.2 Hz, 1 H), 7.27 (m, 1 H), 3.64 (s, 3 H), 3.24 (s, 3 H), 3.15 (d, J=5.7 Hz, 2 H), 2.44 (m, 1 H), 2.00 (ddd, J=19.5, 10.4, 2.4 Hz, 1 H), 1.74 (m, 1 H), 1.65 (s, 3 H), 1.61 (m, 1 H), 1.56 (m, 1H).

Provenance & Evidence