Methyl iodide → HCID 68673141, compound

Participants

Reaction Steps

To a stirred mixture of 25 mg (0.62 mmol, 1.2 equiv) of 60% sodium hydride/mineral oil dispersion and 0.047 mL (0.75 mmol, 1.5 equiv) of iodomethane in 1 mL of anhydrous tetrahydrofuran under nitrogen was added a solution of 230 mg (0.50 mmol) of (±)-tert-butyl 2-{[[(9-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl)methyl](isobutyl)amino]-carbonyl}morpholine-4-carboxylate in 1 mL of anhydrous tetrahydrofuran over five minutes. The mixture was stirred at ambient temperature in a sealed flask for three days. The mixture was diluted with 2 mL of saturated sodium bicarbonate solution and extracted with 2×10 mL of ethyl acetate. The extract was washed with 3 mL each of water and brine, dried over sodium sulfate, filtered, and concentrated to give 263 mg of a gum. Purification by flash chromatography (10-50% ethyl acetate in hexanes) gave 171 mg (72%) of product as a solid white foam. MS (m+1)=475.4; H NMR (400 MHz, CDCl3) 7.06 (m, 2H), 6.96 (m, 1H), 4.7 (m, 1H), 4.50 (d, 1H, J 16 Hz), 4.28 (m, 1H), 4.18-4.02 (m, 2H), 3.97-3.80 (m, 2H), 3.50 (m, 1H), 3.31 (d, 3H, J 10 Hz), 3.22 (m, 2H), 2.99 (m, 3H), 2.65 (m, 1H), 2.01 (m, 2H), 1.86 (m, 2H), 1.75 (m, 1H), 1.60 (m, 2H), 1.45 (d, 9H, J 14 Hz), 0.89 (m, 6H).

Provenance & Evidence