Water → HCID 23541998, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl(±)-cis-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (0.576 g, 1.92 mmol) in DMF (4 mL) at 0° C., freshly recrystalized NBS (0.375 g, 2.1 mmol) was added as a solution in DMF (4 mL). The reaction was stirred at 0° C. for 20 min, after which it was warmed to RT. The reaction was stirred at RT for 0.5 h. Water (10 mL) and EtOAc (10 mL) were added. The layers were separated, and the aqueous phase was extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine (2×20 mL) and dried. Concentration afforded a crude brown oil. The crude product was purified by column chromatography (MeOH/CH2Cl2). Tert-butyl(±)-cis-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (550 mg, 75%) was isolated as a brown amorphous solid. 1H NMR (CDCl3, 300 MHz) δ 7.06 (s, 1H), 7.02 (s, 1H), 3.70–3.90 (m, 1H), 3.50–3.70 (m, 1H), 3.00–3.45 (m, 6H), 2.70–2.90 (m, 2H), 1.70–1.90 (m, 2H), 1.48 (s, 9H) ppm.

Provenance & Evidence