[C:1]1([C:7]2[CH:11]=[C:10]([CH:12]=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.C(=O)(O)[O-].[Na+]>C(#N)C.C(O)(=O)C>[C:1]1([C:7]2[CH:11]=[C:10]([CH2:12][N:14]3[CH2:19][CH2:18][CH:17]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:16][CH2:15]3)[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1A solution of the compound prepared in Example 7 (2.00 g), tert-butyl piperidin-4-ylmethylcarbamate (2.72 g) and acetic acid (0.66 mL) in acetonitrile (60 mL) was stirred at room temperature for 30 minutes. Tetramethylammonium triacetoxyborohydride (9.12 g) was added and the reaction was stirred overnight. The reaction was then poured into a saturated aqueous sodium bicarbonate solution and the resulting mixture was extracted three times with ethyl acetate. The combined organics were dried with anhydrous magnesium sulfate and concentrated to a white solid. The solid was triturated with hexane to obtain the title compound (3.90 g) having the following physical data.
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