Dichloromethane → HCID 66603557, compound

Participants

Reaction Steps

To a solution of 4-(benzyloxy)-1-(5-tosyl-5,6,6a,7,8,9,10,12-octahydroindolo[2,3-b]quinolizin-3-yl)-pyridin-2(1H)-one (50 mg, 0.086 mmol) in CH3OH (2 mL) and CH2Cl2 (2 mL) was added NaOH (17 mg, 0.43 mmol). The mixture was stirred at room temperature until complete. The mixture was filtered through a layer of Celite; the filtrate was concentrated; and the resulting oil was purified by flash column chromatography (silica gel, 10% CH3OH in CH2Cl2) to give the free base of the title compound (29 mg, 79%) as a yellow solid. The yellow solid was dissolved in CH3OH (2 mL) and treated with 2 N HCl in Et2O (1 mL). The resulting solid was isolated by filtration and dried under vacuum to give the title compound (18 mg, 57%) as a yellow powder: mp 270-273° C.; 1H NMR (500 MHz, CD3OD) δ 7.59 (d, J=8.0 Hz, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.48-7.35 (m, 6H), 7.03 (dd, J=8.5, 1.5 Hz, 1H), 6.32 (dd, J=7.5, 3.0 Hz, 1H), 6.15 (d, J=2.5 Hz, 1H), 5.19 (s, 2H), 4.74 (d, J=14.5 Hz, 1H), 4.36 (d, J=14.5 Hz, 1H), 3.79 (d, J=13.0 Hz, 1H), 3.69-3.67 (m, 1H), 3.30-3.28 (m, 2H), 3.03 (dd, J=16.5, 10.5 Hz, 1H), 2.36-2.30 (m, 1H), 2.08-1.97 (m, 2H), 1.88-1.70 (m, 3H); ESI MS m/z 426 [M+H]+; HPLC (Method A) 98.5% (AUC), tR=12.99 min.

Provenance & Evidence