Reaktion #345330

Reaktionsgleichung

1,2,3,3a,8,8a-hexahydro-α-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, ethyl ester

4-chlorophenylethyl alcohol

→

1,2,3,3a,8,8a-hexahydro-α-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, 4 -chlorophenylethyl ester

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was gently heated
2. 2
   Temperaturwithout refluxing for 4 hours
3. 3
   SonstigeThe 4-chlorophenylethyl alcohol was removed by distillation under high vacuum
4. 4
   workup.DISSOLUTIONthe crude residue was dissolved in dichloromethane (20 ml)
5. 5
   Waschenwashed successively with two 100 ml portions of saturated ammonium chloride solution, two 100 ml portions of saturated sodium bicarbonate solution and 100 ml of brine
6. 6
   TrocknenThe organic phase was dried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Sonstigepurified
9. 9
   Sonstigethe solvent removed under vacuum

Vorschrift

To a chilled (0° C.) solution of 1,2,3,3a,8,8a-hexahydro-α-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, ethyl ester (1.18 g) in 4-chlorophenylethyl alcohol (31 ml) was added titanium (IV) ethoxide (0.30 ml) under a nitrogen atmosphere with stirring. The mixture was gently heated without refluxing for 4 hours. The 4-chlorophenylethyl alcohol was removed by distillation under high vacuum and the crude residue was dissolved in dichloromethane (20 ml) and washed successively with two 100 ml portions of saturated ammonium chloride solution, two 100 ml portions of saturated sodium bicarbonate solution and 100 ml of brine. The organic phase was dried (Na2SO4) filtered, and purified using preparative HPLC (silica gel, 3% methanol in dichloromethane as the loading solvent and eluent). The appropriate fractions were combined and the solvent removed under vacuum. Concentration of the appropriate fractions yielded 0.87 g of 1,2,3,3a,8,8a-hexahydro-α-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, 4 -chlorophenylethyl ester as an oil.

Quelle