(E)-5H-cyclopenta[b]pyridin-7(6H)-one O-methyl oxime → 6,7-dihydro-5H-cyclopenta(b)pyridin-7-amine

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Reaction Steps

5,6-Dihydro-[1]pyrindin-7-one O-methyl-oxime (4.1 g, 25.28 mmol) and Pd/C (150 mg) were mixed in TFA and then resulting reaction mixture was hydrogenated under 50 psi for 14 hours. Filtration via celite and concentration afforded the desired title amine. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 1.89-2.02 (m, 1H), 2.46-2.58 (m, 1H), 2.89-3.01 (m, 2H), 4.62-4.73 (m, 1H), 7.30-7.37 (m, 1H), 7.77 (d, J=7.62 Hz, 1H), 8.35-8.50 (m, 3H).

Provenance & Evidence