Potassium Cyanide → HCID 54361250, compound

HRID 1154433Notes

Reaction equation

HRID 1154433 reaction equation
[Br:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]3[CH2:23][CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.O[CH2:26][CH:27]1CC1.[C-]#N.[K+]>>[Br:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]3[CH2:23][CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH2:19][CH:20]3[CH2:27][CH2:26]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 9032Potassium CyanideHCID 75644CyclopropanemethanolHCID 54197869HCID 54197869, compound

Product 1

HCID 54361250HCID 54361250, compound

Procedure

A mixture of 12 g (31 mmol) of ethyl (S)-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate, 60 ml (750 mmol) of hydroxymethyl-cyclopropane and 500 mg of powdered potassium cyanide is stirred at 135° for 1.5 hours, the alcohol being simultaneously distilled off over a Hickmann headpiece and a 15 cm Vigreux column. The mixture is evaporated to dryness, the residue is taken up in chloroform, washed with water, dried over magnesium sulphate and evaporated. By recrystallization from ethyl acetate there is obtained cyclopropylmethyl (S)-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 135°-136°.

Workup

  1. distillationthe alcohol being simultaneously distilled off over a Hickmann headpiece
  2. customThe mixture is evaporated to dryness
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customBy recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-176b2081c2bb407588d492fa0a43e475
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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