[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]12[CH2:19][CH:11]([CH2:12][CH:13]([C:15](OC)=[O:16])[CH2:14]1)[CH2:10][N:9]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:8]2.O.[OH-].[Na+]>C1COCC1>[OH:16][CH2:15][CH:13]1[CH2:12][CH:11]2[CH2:19][CH:7]([CH2:8][N:9]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:10]2)[CH2:14]1Lithium aluminum hydride (2.54 g) was suspended in THF (140 mL), and a solution of 3-tert-butyl 7-methyl 3-azabicyclo[3.3.1]nonane-3,7-dicarboxylate (9.49 g) in THF (27 mL) was added dropwise under ice-cooling. The reaction mixture was stirred for 30 min under ice-cooling, and water (2.54 mL) was slowly added dropwise. To the reaction mixture was added dropwise 15% aqueous sodium hydroxide solution (2.54 mL), and then water (7.5 mL) was added, and the mixture was stirred at room temperature for 3 days. The solid was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (8.02 g).
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