Pyrrolidine → HCID 62177350, compound

Participants

Reaction Steps

5.55 g (78.0 mmol) pyrrolidine are added to a solution of 4.70 g (26.1 mmol) 4-methylamino-3-nitro-benzaldehyde in 100 mL THF and the reaction mixture is acidified with glacial acetic acid. 6.36 g (30.0 mmol) NaBH(OAc)3 are added and the reaction mixture is stirred overnight at RT. The mixture is combined with saturated NaHCO3 solution and the aqueous phase is extracted twice with EtOAc. The combined organic extracts are washed with 200 mL semisaturated NaHCO3 solution and dried over MgSO4. The solvent is eliminated i.vac. and further purification is carried out by column chromatography on silica gel (gradient: DCM to DCM/MeOH 9:1).

Provenance & Evidence