[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([NH:9][C:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH2:16][CH3:17])[C:11](OCC)=[O:12])=O.S([O-])([O-])(=O)=O.[Mg+2].C(OCC)C>C1COCC1>[CH3:7][NH:9][C:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH2:16][CH3:17])[CH2:11][OH:12]To a suspension of 900 mg (23.71 mmol) of lithium aluminum hydride (LiAlH4) in 30 mL of anhydrous THF were added dropwise a solution of 3.09 g (13.15 mmol) of 7, previously prepared, in 18 mL of anhydrous THF. After 4 h under reflux, the reaction mixture was allowed to cool to room temperature and an additional amount of lithium aluminum hydride (900 mg) was introduced. Reflux was maintained for 4 h then an aqueous saturated solution of magnesium sulfate was slowly added at −10° C. under vigorous stirring until formation of a precipitate. The solid was filtered and washed several times with THF. The organic solvent was evaporated under reduced pressure until obtaining of an aqueous solution. The solution was added with 100 mL of diethyl ether and the organic layer was dried over sodium sulfate. Evaporation of the solvent afforded 1.84 g of 8 as a yellow oil. (78% yield).
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