Cyclohexanol → HCID 53949242, compound

HRID 1154431Notes

Reaction equation

HRID 1154431 reaction equation
[Br:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][C:19]([CH3:22])(C)[CH3:20])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:27]1(O)[CH2:32]CCC[CH2:28]1>CCO.CCO.CCO.CCO.[Ti]>[Br:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH:19]3[CH2:20][CH2:32][CH2:27][CH2:28][CH2:22]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7966CyclohexanolHCID 107926Bretazenil

Product 1

HCID 53949242HCID 53949242, compound

Reagents, catalysts & solvents 1

HCID 2724286Titanium(IV)ethoxideCatalyst

Procedure

A mixture of 10 g (24 mmol)of tert.butyl (S)-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate, 30 g (300 mmol) of cyclohexanol and 1.80 g (8 mmol) of tetraethyl orthotitanate is stirred at 125° overnight, the solution obtained is evaporated to dryness, the residue is taken up in chloroform and stirred for 0.5 hour with 40 ml of a saturated potassium fluoride solution. The resulting emulsion is filtered through siliceous earth, the organic phase is separated, washed with water, dried over magnesium sulphate and evaporated. By recrystallization of the residue from ethyl acetate there is obtained cyclohexyl (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 167°-168°.

Workup

  1. customthe solution obtained
  2. customis evaporated to dryness
  3. stirringstirred for 0.5 hour with 40 ml of a saturated potassium fluoride solution
  4. filtrationThe resulting emulsion is filtered through siliceous earth
  5. customthe organic phase is separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customBy recrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-41de5c24b6c64456b8ee9e96eb674d68
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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