[OH-].[Na+].[C:3](OC(=O)C)(=[O:5])[CH3:4].O1CCCC1.Br.[CH2:16]1[CH2:20][O:19][C:18]2[CH:21]=[CH:22][C:23]3[CH2:24][CH2:25][CH:26]([CH2:28][CH2:29][NH2:30])[C:27]=3[C:17]1=2>O>[CH2:16]1[CH2:20][O:19][C:18]2[CH:21]=[CH:22][C:23]3[CH2:24][CH2:25][CH:26]([CH2:28][CH2:29][NH:30][C:3](=[O:5])[CH3:4])[C:27]=3[C:17]1=2
Aqueous 1N sodium hydroxide solution (1.5 ml) and acetic anhydride (0.050 ml, 0.528 mmols) were added to a tetrahydrofuran (1.5 ml) solution of 2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine hydrobromide (0.10 g, 0.352 mmols), and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with a saturated saline solution, then dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from isopropyl ether/hexane to obtain 0.057 g (yield: 66%) of the target compound.
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