反应详情

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.

1. concentrationconcentrated
2. customtriturated with 1N NaOH
3. extractionThe basic solution was extracted with ether and ethylacetate
4. washThe organics were washed with water and brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. concentrationThe filtrate was concentrated
9. custompurified by silica gel chromatography (50% ethylacetate/hexanes)