Acetic Acid → (3aR,7aS)-rel-tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

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Reaction Steps

A mixture of tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate (2.45 g, 11.23 mmol) and palladium hydroxide on carbon (20%, 1 g, 1.424 mmol) in ethanol (8 ml)/acetic acid (16 mL) was hydrogenated at 50 psi and 60° C. overnight. The reaction mixture was filtered through celite. Solvent was evaporated in vacuo and the residue was diluted with dichloromethane and washed with saturated sodium bicarbonate. The aqueous layer was extracted with dichloromethane two more times. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo, The crude was be used without purification. tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (1.896 g) was obtained as a colorless oil.

Provenance & Evidence