6H-Pyrrolo[3,4-b]pyridine-6-carboxylic acid, octahydro-, 1,1-diMethylethyl ester

1059172-92-7

186203-81-6

The general procedure for the synthesis of tert-butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate from tert-butyl 5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate is as follows: tert-butyl 5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate (1.50 g) was dissolved in ethylene glycol monomethyl ether and a catalytic amount of 10% Pd/C. The reaction suspension was heated to 70 °C and stirred under hydrogen atmosphere for 6 hours. Upon completion of the reaction, the mixture was cooled to room temperature, poured into 100 mL of water and extracted with dichloromethane (50 mL x 3). The organic phases were combined, dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuum to afford tert-butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate as a light yellow oil (0.95 g, 65.00% yield). The crude product was used directly in the subsequent reaction without further purification. The structure of the compound was confirmed by the following spectral data: mass spectrum (ESI, positive ion mode) m/z: 227.2 ([M+H]+).