[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]=[CH:20][N+:21]([O-])=O)=[CH:17][C:16]=1[O:26][CH3:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[CH2:7]([O:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]=[CH:20][NH2:21])=[CH:17][C:16]=1[O:26][CH3:27])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1A stirred suspension of LAH (8.0 g, 0.21 mol) in THF (300 mL) is cooled in an ice bath and a solution of 4-benzyloxy-3-methoxynitrostyrene (15.0 g, 52.6 mmol) in THF (300 mL) is added dropwise. The green reaction mixture is allowed to warm to room temperature over 0.5 h, and is then refluxed for 4 h. The grey reaction mixture is treated successively with water (8 mL), 15% aqueous NaOH (8 mL), and water (24 mL). The resulting gray suspension is stirred at 50° C. for 20 min. The resulting yellow suspension is filtered, and the residue is washed with EtOAc. The combined filtrates are evaporated to provide the title compound as yellow oil which is used without further purification.
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