Water → HCID 57270949, compound

Participants

Reaction Conditions

Reaction Steps

Under anhydrous conditions, 4b,5,9b,10-tetrahydro-2-methoxy-1,3-dimethylindeno[1,2-b]indole (76 mg, 0.29 mmol) was dissolved in dry dichloromethane (DCM, 1 cm3) into which a small amount of ethanol had been added. The solution was cooled to -78° C., and a solution of boron tribromide in DCM (0.5 cm3 of 1M solution) added. The reaction was slowly warmed to room temperature, reaction occurring at 0° C. After 30 minutes at 10° C., water (1 cm3) was added cautiously, and the reaction stirred for 15 minutes. The mostly solid material was exhaustively extracted between DCM and a saturated solution of sodium bicarbonate. The DCM layer was dried (Na2SO4), and filtered through a pad of flash silica to yield a colourless solid. Yield: 73 mg, 100% .M.p. 178°-180° (dec). 1H NMR (CDCl3) δ: 7.16 (1H, d, J = 7.3 Hz), 6.99 (1H, ddm), 6.94 (1H, s), 6.73 (1H, ddm, J=7.3, 1.1 Hz), 6.60 (1H, d, J=7.7 Hz), 5.20 (1H, d, J=8.4 Hz), 4.4 (2H, br), 4.15 (1H, ddm), 3.38 (1H, dd, J=16.1, 8.3 Hz), 3.09 (1H, dd, J=16.2 Hz), 2.21 (3H, s), 2.12 (3H, s).

Provenance & Evidence