Sodium Hydroxide → tert-Butyl 7-(2-oxo-4-phenethylpiperazin-1-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

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Reaction Steps

tert-Butyl 7-(2-oxo-4-phenethylpiperazin-1-yl)-5-tosyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (450 mg, 0.716 mmol) and NaOH (800 mg, 20 mmol) were stirred in MeOH/CH2Cl2 (5 mL/5 mL) for 16 h. The mixture was partitioned between CH2Cl2 and water and the organic layer removed, dried and concentrated. The residue was purified by column chromatography (40 g ISCO column eluting with methylene chloride and a 10:1 methanol/ammonium hydroxide mixture; gradient 100% methylene chloride to 90% methylene chloride) to provide the title compound (160 mg, 47%) as a white powder: 1H NMR (500 MHz, DMSO-d6) δ 10.95 (s, 1H), 7.35 (d, J=8.2 Hz, 1H), 7.32-7.25 (m, 4H), 7.22-7.17 (m, 2H), 6.88-6.86 (dd, J=8.3, 1.8 Hz, 1H), 4.51 (s, 2H), 3.69 (t, J=5.6 Hz, 2H), 3.64 (t, J=5.3 Hz, 2H), 3.33 (m, 2H), 2.88-2.83 (m, 2H), 2.83-2.74 (m, 4H), 2.69-2.63 (m, 2H), 1.43 (s, 9H).

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