Methyl iodide → HCID 11998562, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N,N-diisopropylamine (0.60 g, 0.83 mL, 5.9 mmol) in dry THF (5 mL) was cooled to −78° C. and n-butyllithium (2.36 mL, 2.5M in hexane, 5.9 mmol) was added dropwise. The reaction mixture was allowed to warm to 0° C., stirred for 15 minutes and cooled to −78° C. A suspension of Example 6 (1.4 g, 5.9 mmol) in THF (5 mL) was added slowly. The reaction mixture was warmed to 0° C. and stirred for 10 min at 0° C. before dropwise addition of methyl iodide (0.84 g, 0.37 mL, 5.9 mmol). A solid formed immediately. The reaction mixture was allowed to warm slowly to r.t. The solid was filtered, washed with THF and then purified by column chromatography (SiO2, 1:3 EtOAc/hexane) to give the title compound (0.20 g, 13%) as a white solid. δH (DMSO-d6) 3.70 (4H, t, J 4.9 Hz), 3.54 (4H, t, J 4.9 Hz), 2.80-2.72 (2H, m), 2.55-2.45 (1H, m), 2.15-2.09 (1H, m), 1.82-1.72 (1H, m), 1.10 (3H, d, J 6.9 Hz). LCMS (ES+) 253.0 (M+H)+.

Provenance & Evidence