Reaktion #366168

Reaktionsgleichung

2-allyloxy-4,6,7-trichlorobenzo[de]isoquinoline-1,3-dione

(S)-pyrrolidin-3-ylcarbamic acid tert-butyl ester

triethylamine

→

title compound

Ausbeute 57.6%

(S)-[1-(2-Allyloxy-4,7-dichloro-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin 6-yl)pyrrolidin-3-yl]carbamic acid tert-butyl ester

Ausbeute 57.6%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed in vacuo
2. 2
   Sonstigethe residue partitioned between water and dichloromethane
3. 3
   SonstigeThe organic layer was dried
4. 4
   Sonstigeevaporated in vacuo
5. 5
   SonstigeThe residue was chromatographed on silica gel (ICN 230-400 mesh)
6. 6
   Wascheneluting with dicholromethane/ethyl acetate (80:20)

Vorschrift

A suspension of 2-allyloxy-4,6,7-trichlorobenzo[de]isoquinoline-1,3-dione (0.44 g, 1.2 mmol, from Example I4), (S)-pyrrolidin-3-ylcarbamic acid tert-butyl ester (0.3 g, 1.5 mmol), triethylamine (0.2 g, 2.0 mmol), and 20 mL of acetonitrile was stirred at room temperature for 6 hours. The solvent was removed in vacuo and the residue partitioned between water and dichloromethane. The organic layer was dried and evaporated in vacuo. The residue was chromatographed on silica gel (ICN 230-400 mesh) eluting with dicholromethane/ethyl acetate (80:20) to give 0.35 g of the title compound, mp 123-125° C.

Quelle