[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[N:11][C:12]([CH:21]3[CH2:26][CH2:25][N:24]([C:27](OCC4C=CC=CC=4)=O)[CH2:23][CH2:22]3)=[CH:13][C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:38][C:2]([F:1])([F:37])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[N:11][C:12]([CH:21]3[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]3)=[CH:13][C:14]=2[C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)[CH:6]=[CH:7][CH:8]=1Under Ar, a solution of 15 (0.73 g, 1.4 mmol) in THF (175 mL) was treated with LAH (0.37 g, 9.7 mmol). After addition, the reaction was heated at 60° C. After 2 h, the reaction was cooled to room temperature and treated with saturated Na2SO4 until a suspension results. The reaction mixture was filtered and the filtrate washed with EtOAc. The organic was washed with H2O, brine, dried, filtered and concentrated to dryness. The residue was treated with Et2O-hexanes, filtered and dried to yield 0.3 g of 16; mp 188-9° C.
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