Reaction #95802

Reaction equation

potassium cyanide

ethyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

potassium cyanide

→

isopropyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

Solvents

2-propanol

2-propanol

Conditions

Workup

1. 1
   OtherThe mixture is evaporated in vacuo
2. 2
   Temperatureheated
3. 3
   Temperatureunder reflux for 22 hours
4. 4
   OtherAfter evaporation in vacuo
5. 5
   workup.ADDITIONthe residue is treated with water
6. 6
   Extractionextracted three times with 30 ml of chloroform each time
7. 7
   WashThe combined chloroform phases are washed three times with 20 ml of water each time
8. 8
   Dryingdried over magnesium sulphate
9. 9
   Otherevaporated
10. 10
    OtherAfter recrystallisation from ethyl acetate/n-hexane

Procedure

934 mg (3 mmol) of ethyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate are stirred at 60° C. for 48 hours with 198 mg (3 mmol) of potassium cyanide in 30 ml of dry 2-propanol. The mixture is evaporated in vacuo. The residue is treated with 30 ml of 2-propanol and 198 mg (3 mmol) of potassium cyanide and heated to boiling under reflux for 22 hours. After evaporation in vacuo, the residue is treated with water and extracted three times with 30 ml of chloroform each time. The combined chloroform phases are washed three times with 20 ml of water each time, dried over magnesium sulphate and evaporated. After recrystallisation from ethyl acetate/n-hexane, there is obtained isopropyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 207°-208° C.

Source