Sodium borohydride → tert-Butyl 3-(hydroxymethyl)-1H-pyrrolo(2,3-b)pyridine-1-carboxylate

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Reaction Steps

To a solution of 1-(tert-butoxycarbonyl)-3-formyl-7-azaindole (2.5 g, 10.2 mmol) in 16 mL EtOH was added NaBH4 (115 mg, 3.05 mmol). The reaction was stirred at ambient temperature for 4 h, concentrated and triturated with 1N NaOH. The basic solution was extracted with ether and ethylacetate. The organics were washed with water and brine, then dried over Na2SO4, filtered and concentrated. The filtrate was concentrated and purified by silica gel chromatography (50% ethylacetate/hexanes) to give tert-butyl 3-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (44%). LCMS [M-tert-Bu]+=191.1.

Provenance & Evidence