Sodium Hydroxide → 9-benzyl-3-hydroxymethyl-beta-carboline

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Reaction Steps

Compound 33 (3.3 g, 10 mmol) was mixed with anhydrous THF (100 ml). The mixture was added dropwise to a mixed solution of LiAlH4 (1.2 g, 30 mmol) and anhydrous THF (100 ml). After that, the mixture was refluxed for 10 h. Then the mixture was cooled to room temperature. 10% NaOH (50 ml) was added into the mixture and then stirred for 20 minutes. The mixture was extracted with ethyl acetate, the organic phases were combined and washed with water and brine, dried over anhydrous sodium sulfate, filtered, evaporated and purified by silica gel column chromatography with ethyl acetate as the eluent. Upon recrystallization, white solids (1.5 g, 52%) were obtained, mp 120-122° C.

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