Reaktion #48481

Reaktionsgleichung

hydrochloric acid

7-(1H-Indole-3-carbonyloxy)-9-methoxycarbonylmethyl-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

potassium tert-butoxide

AcOEt MeOH

→

5-(1H-Indole-3-carbonyloxy)-10-oxo-8-aza-tricyclo[5.3.1.03,8]undecane-9-carboxylic acid methyl ester

Ausbeute 81.0%

Lösungsmittel

water

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe product is extracted with dichloromethane
2. 2
   Sonstigethe organic phase is dried
3. 3
   Sonstigeevaporated

Vorschrift

7-(1H-Indole-3-carbonyloxy)-9-methoxycarbonylmethyl-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester (4.87 gr, 11.75 mmol) dissolved in THF (150 mL) is added to a mixture of potassium tert-butoxide (5.26 gr, 46.9 mmol) in THF (150 mL), under nitrogen. The resulting suspension is stirred for 3 h, until the starting product has been used up as shown by thin-layer chromatography (AcOEt/MeOH 9:1). When the reaction is considered completed, water is added and the pH adjusted to 7.5 with 1 M hydrochloric acid. The product is extracted with dichloromethane, and the organic phase is dried and evaporated, to provide 5-(1H-Indole-3-carbonyloxy)-10-oxo-8-aza-tricyclo[5.3.1.03,8]undecane-9-carboxylic acid methyl ester as a solid (3.63 gr, 81%).

Quelle