Water → HCID 12696796, compound

Participants

Reaction Steps

A flame dried flask was charged with sodium hydride (60 mg, 2.5 mmol), and tetrahydrofuran (THF) (5 cm3) protected under an atmosphere of nitrogen. To the stirring suspension was added cis-4b,5,9b,10-tetrahydroindeno[1,2-b]indole (500 mg, 2.4 mmol) in THF (5 cm3) dropwise. The reaction was stirred for 1 hour, a pink colour developing. Iodomethane (0.2 cm3) was added, and the solution was stirred overnight. Water (5 cm3) was added, and the THF removed in vacuo. The colourless solid thus obtained was filtered, and dried in a vacuum desiccator. The product was dissolved in 5% ethyl acetate petrol (60°-80° C.) and filtered through a pad of flash silica. After evaporation of the solvent in vacuo, the title compound was obtained as a colourless solid. Yield: 450 mg (85%). M.p. 76°-77° C. 1H NMR (CDCl3) δ: 3.0 (3H, s,), 3.1 (1H, dd,), 3.4 (1H, dd,), 4.1 (1H, ddd,), 4.9 (1H, d,), 6.4 (1H, d,), 6.7 (1H, dd,), 7.1-7.5 (6H, m,).

Provenance & Evidence