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

HRID 2198730Notes

Reaction equation

HRID 2198730 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:5]2[C@@H:4]2[CH2:21][CH2:22][CH2:23][N:3]12.[C-:24]#N.[K+]>CC(O)C>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([O:18][CH:19]([CH3:24])[CH3:20])=[O:17])=[C:5]2[C@@H:4]2[CH2:21][CH2:22][CH2:23][N:3]12

Participants

4

Reactant 2

HCID 9032Potassium Cyanide2×HCID 10041121Ethyl (7S)-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate

Product 1

HCID 54047224isopropyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

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 was washed three times with 20 ml of water each time, dried over magnesium sulphate and evaporated. After recrystalisation 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.

Workup

  1. customThe mixture is evaporated in vacuo
  2. temperatureheated
  3. temperatureunder reflux for 22 hours
  4. customAfter evaporation in vacuo
  5. additionthe residue is treated with water
  6. extractionextracted three times with 30 ml of chloroform each time
  7. washThe combined chloroform phases was washed three times with 20 ml of water each time
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customAfter recrystalisation from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-8b9df37eb80645f0a9be31cd1aafe58d
Source dataset
uspto-grants-1982_11
Patent number
US04359420

Reaction notes

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