[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]2[O:18][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)=[N:16][C:15]=2[CH:26]=1)=O.O.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:25][C:21]1[CH:20]=[C:19]([C:17]2[O:18][C:14]3[CH:13]=[CH:12][C:11]([CH2:9][OH:8])=[CH:26][C:15]=3[N:16]=2)[CH:24]=[CH:23][CH:22]=1Lithium aluminum hydride was added to 100 ml THF and stirred for 10 minutes and cooled in an ice bath. A solution of Compound 69A (9.06 g, 33.4 mmol) in 200 ml THF was added dropwise over ½ hr to the lithium aluminum hydride solution and stirred for 2 h. A saturated solution of water/sodium sulfate decahydrate was added until gas evolution ceased and a heavy white precipitate formed. The reaction was stirred for 30 minutes more and filtered through Celite®, extracted into 2×200 ml ethyl acetate, washed with 1×50 ml brine dried over anhydrous sodium sulfate, and filtered through silica. The product was eluted with 300 ml ethyl acetate and concentrated to give a cream colored solid. MS m/z 244 (M+1).
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