Sodium Hydroxide → HCID 20576952, compound

Participants

Reaction Steps

Tert-butyl(±)-cis-2-(2-chlorophenyl)-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (45.1 mg, 0.11 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 1M 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 (29.3 mg, 86%) as a pale yellow amorphous solid. 1H NMR (CDCl3, 300 MHz) δ 7.42 (dd, 1H, J=1.4, 7.3 Hz), 7.16–7.33 (m, 3H), 7.02 (s, 1H), 6.96 (s, 1H), 3.69 (dt, 1H, J=1.4, 8.1 Hz), 3.15–3.50 (m, 5H), 3.06 (dt, 1H, J=3.2, 12.3 Hz), 2.82–2.97 (m, 3H), 1.78–1.93 (m, 2H) ppm. MS (CI, NH3): 311 (base, M+H).

Provenance & Evidence