HCID 59305171, compound → HCID 59305202, compound

Participants

Reaction Steps

3′-Methyl-1′-(phenylmethyl)-1,2-dihydrospiro[indole-3,4′-piperidine] (10 mmol, 2.9 g), acetic acid (30 mL) and Pd/C (5%, 600 mg) were added to a Parr bottle. The mixture was subjected to hydrogen gas at 30 psi for 20 h, after which time the solution was filtered over celite, concentrated and purified by reverse phase chromatography, 10-50% acetonitrile/water (0.1% TFA) over 14 min to give 3′-methyl-1,2-dihydrospiro[indole-3,4′-piperidine] (750 mg) as the TFA salt as an off white solid. MS (ES) m/e 203 [M+H]+ 1H NMR (400 MHz, DMSO-d6) δ ppm 0.62 (d, J=7.03 Hz, 3H) 1.83 (d, J=14.31 Hz, 1H) 2.00 (td, J=13.87, 4.14 Hz, 1H) 2.13 (dd, J=7.15, 4.39 Hz, 1H) 2.77 (d, J=11.80 Hz, 1H) 2.94 (d, J=11.54 Hz, 1H) 3.17 (d, J=1.51 Hz, 1H) 3.31 (d, J=13.30 Hz, 1H) 3.40 (d, J=10.79 Hz, 1H) 3.61 (d, J=11.04 Hz, 1H) 6.79 (d, J=7.78 Hz, 1H) 6.88 (t, J=7.28 Hz, 1H) 7.03 (d, J=7.28 Hz, 1H) 7.12 (t, J=7.15 Hz, 1H) 8.74 (br. s., 1H) 8.87 (br. s. 1H).

Provenance & Evidence