[O:1]=[C:2]([CH2:13][CH3:14])[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]([NH2:12])=O)[CH2:6][CH2:5]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:12][CH2:10][CH:7]1[CH2:6][CH2:5][N:4]([CH2:3][CH:2]([OH:1])[CH2:13][CH3:14])[CH2:9][CH2:8]1To a stirred mixture of 1-(2-oxobutyl)piperidine-4-carboxamide (Example 13, Step 1, 1.60 g, 8.07 mmol) in tetrahydrofuran (200 mL) was added portionwise lithium aluminum hydride (920 mg, 24.21 mmol) at room temperature. The resulting mixture was refluxed for 5 h and cooled to room temperature. The mixture was treated with water (1.8 mL), 2N aqueous sodium hydroxide (3.6 mL) and water (1.8 mL). The mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo to afford 1.64 g (97%) of the title compound as colorless oil.
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