Water → methyl 2,3-dihydro-1H-indole-5-carboxylate

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Reaction Steps

To a solution of 1H-Indole-5-carboxylic acid methyl ester (1 g, 5.71 mmol) in 10 mL of acetic acid at 0° C., was added sodium cyanoborohydride (1.08 g, 17.18 mmol) over 5 minutes. The mixture was stirred at room temperature for 1 h. Water (3 mL) was added and all the solvents were removed under vacuum. The residue was dissolved in ethyl acetate (150 mL) and saturated NaHCO3 (150 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3×75 mL). The combined extracts were washed with brine (150 mL), dried, filtered and evaporated. The residue was purified by flash chromatography (0-50% ethyl acetate in hexane+0.1% triethylamine) to afford 0.99 g (99%) of 19a.

Provenance & Evidence