Reaction #48482

Reaction equation

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

LiCl

AcOEt MeOH

→

1H-Indole-3-carboxylic acid 10-oxo-8-aza-tricyclo[5.3.1.03,8]undec-5-yl ester

Yield 83.0%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   OtherOnce 4 hours
2. 2
   workup.WAITthe mixture is left
3. 3
   Temperatureto cool
4. 4
   OtherVolatile substances are evaporated at low pressure
5. 5
   workup.DISSOLUTIONthe residue is dissolved in dichloromethane (150 mL)
6. 6
   WashThis is washed with a saturated aqueous solution of NaCl (70 mL)
7. 7
   Dryingthe organic phase is dried over magnesium sulphate
8. 8
   Otherevaporated

Procedure

A mixture of 3.1 gr (8.1 mmol) of 5-(1H-Indole-3-carbonyloxy)-10-oxo-8-aza-tricyclo[5.3.1.03,8]undecane-9-carboxylic acid methyl ester and LiCl (0.69 gr, 16.23 mmol) in dimethylformamide (90 mL) is heated to 140° C. Once 4 hours have elapsed, and after checking by thin-layer chromatography (AcOEt/MeOH 9:1) that the reaction has been completed, the mixture is left to cool. Volatile substances are evaporated at low pressure and the residue is dissolved in dichloromethane (150 mL). This is washed with a saturated aqueous solution of NaCl (70 mL), and the organic phase is dried over magnesium sulphate and evaporated, to provide crude 1H-Indole-3-carboxylic acid 10-oxo-8-aza-tricyclo[5.3.1.03,8]undec-5-yl ester as a solid (2.18 gr, 83%).

Source