Chlorosuccinimide → HCID 68735147, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 1′-benzyl-4-((tert-butoxycarbonylamino)methyl)spiro[indoline-3,4′-piperidine]-1-carboxylate (115 mg, 0.227 mmol) in DCM (2 mL) was added 1-chloropyrrolidine-2,5-dione (NCS) (66 mg, 0.50 mmol). The reaction mixture was stirred at about room temperature for 48 hours. The reaction mixture was diluted with DCM, washed with saturated aqueous NaHCO3 solution and brine, dried and concentrated. The residue was dissolved in DCM (2 mL) and treated with 4N HCl in dioxane (0.5 mL) overnight. The solvents were evaporated. The residue was taken up in DCM and basidified with saturated aqueous NaHCO3 solution. The aqueous phase was extracted with DCM. The combined organic layers were washed with brine, dried and concentrated to give (1′-benzyl-5-chlorospiro[indoline-3,4′-piperidine]-4-yl)methanamine (40 mg, 52%) as an oil, which was used in the next step without further purification. LCMS (APCI+) m/z 342, 344 [M+H]+; Rt=1.71 min.

Provenance & Evidence