Sodium Hydroxide → HCID 20576996, compound

Participants

Reaction Steps

4,5,7,8,9,10-Hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole from Example 1 (0.50 g, 2.14 mmol) was stirred under N2 in TFA (15.5 mL) at 0° C. for 10 minutes. NaBH4 (0.44 g, 6.4 mmol) was added slowly keeping the temperature below 2° C. The reaction was allowed to warm to room temperature and stirred overnight. Ice chips were then added and the reaction basified to pH 12 with 50% aqueous NaOH. The aqueous layer was then extracted with CHCl3 (3×20 mL). The combined extracts were washed with brine, H2O and dried (Na2SO4) and evaporated affording the title compound (0.42 g, 100%). 1H NMR (CDCl3, 300 MHz) δ 6.94 (d, 1H, J=7.7 Hz), 6.88 (d, 1H, J=6.9 Hz), 6.63 (t, 7.3, 1H, J=7.3 Hz), 3.64 (dt, 1H, J=8.0, 1.5 Hz), 3.29-3.5 (m, 2H), 3.05-3.29 (m, 3H), 3.03 (dd, 1H, J=11.7, 3.6 Hz), 2.72-3.02 (m, 2H), 1.66-1.90 (m, 2H) ppm.

Provenance & Evidence