[H-].[Al+3].[Li+].[H-].[H-].[H-].O[N:8]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C:10]21[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19][CH2:18]2.C1COCC1.[OH-].[Na+]>C(OCC)C.O>[CH3:23][C:20]1([CH3:24])[O:19][CH2:18][C:10]2([CH2:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]2[NH2:8])[CH2:22][O:21]1To a suspension of 384 mg of lithium aluminum hydride in 22 ml of diethyl ether were added 0.5 g of N-hydroxy-2,2-dimethylspiro[1,3-dioxane-5,2′-inden]-1′(3′H)-imine and 5 ml of THF under ice-cooling, followed by stirring at 40° C. for 8 hours. 0.55 ml of water, 0.55 ml of a 15% aqueous sodium hydroxide solution, and 1.65 ml of water were added thereto under ice-cooling. After filtration through Celite, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 146 mg of 2,2-dimethyl-1′,3′-dihydrospiro[1,3-dioxane-5,2′-inden]-1′-amine.
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