Sodium borohydride → (3-(Hydroxymethyl)-1H-indol-6-yl)(morpholino)methanone

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Reaction Steps

Sodium borohydride (2.2 g, 58.34 mmol) was added at 0° C. portion wise to a suspension of 6-(morpholine-4-carbonyl)-1H-indole-3-carbaldehyde (5 g, 19.44 mmol) in methanol (106 mL) and the mixture was stirred at room temperature for 3 h. The methanol was removed under vacuum whereby the temperature was kept below <35° C. The residue was diluted with water (100 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine, dried over sodium sulfate and evaporated. Washing of the remnant with ether provided the product as white solid. Yield: 4 g (79% of theory)

Provenance & Evidence