Octahydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester

Synthesis

The general procedure for the synthesis of 1-Boc-1H-octahydropyrrolo[3,2-c]pyridine from 1-Boc-1H-pyrrolo[3,2-c]pyridine was as follows: 1H-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (2.55 g) was dissolved in a mixed solvent of ethylene glycol monomethyl ether (40 mL) and acetic acid (1 mL), and catalytic amounts of palladium hydroxide/ carbon (Pd(OH)2/C). The reaction suspension was heated at 70 °C for 24 h under hydrogen (2.0 MPa) atmosphere. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under vacuum to remove the solvent. The resulting residue was purified by silica gel column chromatography with the eluent being a solvent mixture of dichloromethane and methanol (10:1, v/v) to afford the final target product 1-Boc-1H-octahydropyrrolo[3,2-c]pyridine as a viscous liquid (2.64 g, 100.00% yield).

References

[1] Patent: WO2013/71697, 2013, A1. Location in patent: Paragraph 00276
[2] Patent: US2014/228361, 2014, A1. Location in patent: Paragraph 0418-0419