1,1-Dichloroethane → tert-butyl 5-(3-amino-2-chloro-5-cyanophenyl)octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Participants

Reaction Steps

tert-butyl 5-(3-((tert-butoxycarbonyl)amino)-2-chloro-5-cyanophenyl)octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (358 mg, 0.751 mmol) was treated with 25% TFA in dichloroethane (2 ml, 6.49 mmol) at room temperature for 1 h. Solvent was evaporated in vacuo and the residue was diluted with dichloromethane and washed with water and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo, the crude intermediate was dissolved in dichloromethane (10 mL). Triethylamine (0.209 ml, 1.501 mmol) and BOC anhydride (0.261 ml, 1.126 mmol) were added subsequently. The reaction mixture was stirred at room temperature for 1 h and the reaction was complete. The reaction mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate. The aqueous layer was extracted with dichloromethane two more times. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo, the crude product was purified by flash chromatography on silica gel using an automated ISCO system (40 g column, eluting with 10-30% ethyl acetate/hexanes) to give tert-butyl 5-(3-amino-2-chloro-5-cyanophenyl)octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (266 mg) as a colorless oil.

Provenance & Evidence