C(O[C:4]([NH:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)=O)C.C(=O)(O)N.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>CCOCC>[CH3:4][NH:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1Under a nitrogen atmosphere, a solution of the carbamate 2-(ethoxycarbonyl-amino)indane (6.07 g, 29.6 mmol) in Et2O (100 mL) is added slowly to a mixture of LiAlH4 (1.70 g, 44.7 mmol) in Et2O (100 ml) chilled at 0°. The resulting mixture is stirred for 18 h and allowed to warm to 20°. The reaction mixture is re-chilled to 0° and treated cautiously with H2O (1.7 mL), 15% NaOH (1.7 mL) and again H2O (5.1 mL). The mixture is stirred for 20 minutes, warming slowly to 20°. The precipitate is vacuum filtered and the filtrate extracted into 1N HCl. The acid solution is washed with fresh Et2O, then basified with cold 1N NaOH. The cloudy mixture is extracted with Et2O, washed with saturated brine, dried over Na2SO4, is filtered and concentrated to an oil.
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