Lithium Hydroxide → 1-[(tert-butoxy)carbonyl]-1H,2H,3H-pyrrolo[2,3-b]pyridine-2-carboxylic acid

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Reaction Steps

A suspension of 2,3-dihydro-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (1 g) and lithium hydroxide (0.25 g) in 6 ml THF, 3 ml MeOH and 3 ml water was stirred 0.5 h at rt. The reaction mixture was poured onto 1M HCl/ice and washed three times with dichloromethane. The aqueous layer was neutralized with 1M NaOH, evaporated to dryness and purified by chromatography (silica gel, dichloromethane/methanol, 4/1) to yield 2,3-dihydro-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester as a white solid (400 mg). MS: 263.4 (M−H)−

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