[C:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:20][N:21]=[N+]=[N-])([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.O>[C:1]([N:8]1[CH2:9][CH2:10][C:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)([CH2:20][NH2:21])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]A 25-mL, round-bottomed flask was charged with Intermediate 1c (0.259 g, 0.803 mmol), 8 mL of THF, and triphenylphosphine (0.32 g, 0.884 mmol). The mixture was stirred at room temperature for 3.5 h and then 0.10 mL of water was added. The resulting reaction mixture was stirred at room temperature for 66 h, and then diluted with ethyl acetate and water. The layers were separated, and the organic phase was washed with water and saturated sodium chloride solution, dried over potassium carbonate, filtered and concentrated. The crude product was purified by column chromatography (gradient elution: 1:4 ethyl acetate-hexane, 9:1 ethyl acetate-methanol, and then 100% methanol) to give the free amine (0.063 g) as a clear oil.
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