Water → HCID 9924971, compound

Participants

Reaction Steps

To a solution of 10-benzoyl-3,3-dimethyl-7,8,9,10,11,12-hexahydro-3H-azepino[4,5-b]pyrano[3,2-e]indole (0.115 g, 0.31 mmol) in tetrahydrofuran (5.0 mL) was added lithium aluminum hydride (0.125 g, 3.10 mmol). The resulted mixture was stirred at room temperature for 16 h. Water (0.13 mL), 15% sodium hydroxide solution (0.13 mL) and water (0.39 mL) were added sequentially. The mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to dryness. The residue was subjected to prep TLC (25% EtOAc/hexane, 1% Et3N) to afford 0.067 g (60%) of light yellow solid as the title compound: 1H NMR (300 MHz, CDCl3) δ 7.68, 7.47-7.30, 7.06-7.02, 6.69, 5.63, 3.85, 3.18-3.16, 3.05-2.88, 1.49; 13C NMR (DMSO-d6) δ 147.3, 139.5, 138.2, 130.8, 129.4, 129.2, 128.7, 127.5, 124.7, 120.9, 113.5, 113.2, 111.9, 110.0, 75.0, 61.4, 55.8, 54.0, 28.6, 27.4, 26.2; MS (ESI+) m/z 373 (M++H).

Provenance & Evidence