Sodium Hydroxide → HCID 86641005, compound

Participants

Reaction Steps

To a solution of 1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indole]-2′,5(1′H,6H)-dione (0.25 g, 0.66 mmol) in methanol (10 mL) and tetrahydrofuran (10 mL) were added hydroxylamine hydrochloride (0.92 g, 13.3 mmol) and sodium acetate (1.09 g, 13.3 mmol). The reaction mixture was stirred for 48 h at ambient temperature. To the reaction mixture was added 1 N sodium hydroxide to adjust pH>9. The mixture was extracted with ethyl acetate (2×50 mL). The combined organic solution was washed with water and brine, then dried over sodium sulfate, filtered and concentrated to afford 1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indole]-2′,5(1′H,6H)-dione 5-oxime (0.25 g, 96%) as a colorless solid: mp 82-100° C.; 1H NMR (300 MHz, CDCl3) δ 8.00-7.50 (br, 1H), 7.49-6.83 (m, 5H), 6.52-6.46 (m, 1H), 5.10-4.93 (m, 3H), 4.76-4.69 (m, 1H), 4.30-5.19 (m, 1H), 3.95-3.66 (m, 4H), 2.08-1.60 (m, 4H); MS (ES+) m/z 392.9 (M+1), 414.9 (M+23).

Provenance & Evidence