Nitrogen → HCID 25165894, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione (WO2006086484A1, 8.34 g, 22.6 mmol) in anhydrous THF (400 mL) was purged with N2 and cooled to 0° C. LiAlH4 (226 mL, 1 M in THF, 226 mmol) was added dropwise. The reaction mixture was stirred at 60° C. overnight. The mixture was cooled with an ice-water bath and water (40 mL) added dropwise under N2 to quench excess LiAlH4. Water (500 mL) was added. The mixture was then acidified with 4M HCl to pH<2. 2M NaOH was added to adjust to pH>9. The mixture was extracted with EtOAc (2×800 mL). The combined EtOAc layer was washed with saturated aqueous NaCl solution, dried over Na2SO4 and concentrated to give 1-[(3R,4R)-4-(1H-indol-3-yl)-pyrrolidin-3-yl]-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline as an orange/yellow solid.

Provenance & Evidence