[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[C:13]([CH:14]=[CH:15][N+:16]([O-])=O)=[CH:12][CH:11]=[CH:10][C:9]=1[O:19][CH2:20][CH:21]1[CH2:23][CH2:22]1.O.[OH-].[Na+]>C1COCC1>[Br:7][C:8]1[C:9]([O:19][CH2:20][CH:21]2[CH2:23][CH2:22]2)=[CH:10][CH:11]=[CH:12][C:13]=1[CH2:14][CH2:15][NH2:16]To 0.92 mL (2.2 mmol) lithium aluminum hydride solution (2.4 M in THF) are added dropwise 300 mg (1.01 mmol) 2-bromo-1-cyclopropylmethoxy-3-(2-nitro-vinyl)-benzene (example XX) in 5 mL THF at 0° C. After stirring at 0° C. for 2 h the reaction mixture is quenched by the addition of 36 μL (2.0 mmol) water, 0.50 mL (2.0 mmol) aq. NaOH solution (c=4 mol/L) and 0.11 mL (6.0 mmol) water. The resulting mixture is stirred for 20 min, filtered over celite/Na2SO4 and the filtrate is concentrated by evaporation. The residue is purified by HPLC (ACN/H2O/NH4OH).
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