[C:1]12([CH2:11][NH:12][C:13](=O)[CH2:14][C:15](=[O:20])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:1]12([CH2:11][NH:12][CH2:13][CH2:14][CH:15]([OH:20])[CH2:16][CH:17]([CH3:18])[CH3:19])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2A solution of N-(1-adamantylmethyl)-5-methyl-3-oxohexanamide (1.5 g, 5.1 mmol) in anhydrous THF (15 mL) was added slowly to a suspension of LAH (500 mg, 13.1 mmol) in anhydrous THF (5 mL) under N2 at 0° C. The reaction mixture was heated to 70° C. and stirred at this temperature overnight. Water (0.5 mL) and 10% aq NaOH (0.5 mL) were added to quench the reaction. The resulting slurry was filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on a silica gel column eluted with 10:1 PE/EtOAc to give 1-(1-adamantylmethylamino)-5-methylhexan-3-ol (900 mg, 63.3%). MS (M+1): 280.
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