Sodium Hydroxide → HCID 10109086, compound

Participants

Reaction Steps

Tert-butyl(±)-cis-2-(2,3-dichlorophenyl)-5,6,8,9,11,11a-hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-carboxylate (55 mg, 0.12 mmol) was dissolved in 20% TFA in methylene chloride (4 mL) and was stirred at RT for 2 h. The reaction was solution was cooled to 0° C. and basified with 1 M NaOH until pH >14. The layers were separated. The aqueous phase was extracted the methylene chloride (2×10 ml). The organic layers were washed with brine and dried. Concentration afforded the title compound (43 mg, 100%) as a pale yellow amorphous solid. 1H NMR (CDCl3, 300 MHz) δ 7.37 (dd, 1H, J=2.6, 7.3 Hz), 7.15–7.23 (m, 2H), 6.97 (s, 1H), 6.92 (s, 1H), 3.43–3.46 (m, 1H), 3.31 (dt, 1H, J=4.4, 10.2), 3.03–3.11(m, 2H), 2.81–2.94 (m, 2H), 2.60–2.80 (m, 4H), 2.11–2.20 (m, 2H), 1.89–1.98 (m, 1H), 1.74–1.85 (m, 1H) ppm. MS (CI, NH3): 359 (base, M+H).

Provenance & Evidence