反应详情

温度

50 °C

TFA (2.2 ml, 28 mmol) was added to a stirred solution of tert-butyl 4-formylpiperidine-1-carboxylate (2.00 g, 9.38 mmol), 1-(4-chlorophenyl)hydrazine hydrochloride (1.68 g, 9.38 mmol) and ethanol (0.2 mL) in CHCl3 (200 mL) at about 0° C. The reaction mixture was then stirred at about 50° C. overnight. After cooling, the reaction was quenched by the addition of 10% NH4OH (20 mL) and ice (60 mL). The organic layer was separated. The aqueous layer was extracted with DCM. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to yield tert-butyl 5-chlorospiro[indole-3,4′-piperidine]-1′-carboxylate which was used in the next step without further purification (2.57 g, 85%). LCMS (APCI+) m/z 221, 223 [M+H−Boc]+; Rt=3.67 min.

1. temperatureAfter cooling
2. customthe reaction was quenched by the addition of 10% NH4OH (20 mL) and ice (60 mL)
3. customThe organic layer was separated
4. extractionThe aqueous layer was extracted with DCM
5. washThe combined organic layers were washed with brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated