[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]([C:15]1[NH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][CH:18]=2)([CH3:14])[C:9](OCC)=[O:10].O.[OH-].[Na+]>C1COCC1>[CH3:14][C:8]([C:15]1[NH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][CH:18]=2)([CH3:7])[CH2:9][OH:10]
To a cooled solution of LiAlH4 (1.0 M in THF, 1.1 mL, 1.1 mmol) in THF (5 mL) at 0° C. was added a solution of ethyl 2-methyl-2-(5-nitro-1H-indol-2-yl)propanoate (0.20 g, 0.72 mmol) in THF (3.4 mL) dropwise. After addition, the mixture was allowed to warm up to room temperature and was stirred for 3 h. The mixture was cooled to 0° C. before water (2 mL) was slowly added followed by careful addition of 15% NaOH (2 mL) and water (4 mL). The mixture was stirred at room temperature for 0.5 h and was filtered through a short plug of celite using ethyl acetate. The organic layer was separated from the aqueous layer, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1) to give 2-methyl-2-(5-nitro-1H-indol-2-yl)propan-1-ol (0.098 g, 58%).
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