[NH2:1][CH2:2][CH2:3][CH:4]1[C:16]2[C:15]3[NH:14][C:13](=O)[CH2:12][O:11][C:10]=3[CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH:14]1[CH2:13][CH2:12][O:11][C:10]2[CH:9]=[CH:8][C:7]3[CH2:6][CH2:5][CH:4]([CH2:3][CH2:2][NH2:1])[C:16]=3[C:15]1=2
A solution of 9-(2-aminoethyl)-1,7,8,9-tetrahydro-indeno[5,4-b][1,4]oxazin-2(3H)-one (1.2 g, 5.3 mmol.) in tetrahydrofuran (30 mL) was was cooled with ice, to which was added lithium aluminum hydride (0.8 g, 21.4 mmol.). The mixture was heated for 18 hours under reflux under argon atmosphere. The reaction mixture was cooled, to which were added water (0.8 mL), a 15% aqueous solution of sodium hydroxide (0.8 mL) and water (2.4 mL), successively. The mixture was then stirred for 30 minutes at room temperature. Insolubles were filtered off, and the filtrate was concentrated under reduced pressure. Then, in substantially the same manner as in Example 36, from 2-(1,2,3,7,8,9-hexahydroindeno[5,4-b][1,4]oxazin-9-yl) ethylamine thus obtained and propionic acid, the title compound was produced (yield 250 mg, 51%).
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