Cyclohexanol → HCID 54533391, compound

HRID 1154438Notes

Reaction equation

HRID 1154438 reaction equation
[I: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]>[I: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 10718981HCID 10718981, compound

Product 1

HCID 54533391HCID 54533391, compound

Reagents, catalysts & solvents 1

HCID 2724286Titanium(IV)ethoxideCatalyst

Procedure

5 g (11 mmol) of tert.butyl (S)-11,12,13,13a-tetrahydro-8-iodo-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate, 30 g (300 mmol) of cyclohexanol and 1 g (4 mmol) of tetraethyl orthotitanate are stirred at 125° overnight, the solution is evaporated to dryness and the residue is taken up in chloroform. The solution is then stirred for 0.5 hour with 40 ml of a saturated potassium fluoride solution, the resulting emulsion is filtered over siliceous earth, the organic phase is separated, washed with water, dried over magnesium sulphate and evaporated. By crystallization from ethyl acetate there is obtained cyclohexyl (S)-11,12,13,13a-tetrahydro-8-iodo-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 181°-182°.

Workup

  1. customthe solution is evaporated to dryness
  2. filtrationthe resulting emulsion is filtered over siliceous earth
  3. customthe organic phase is separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customBy crystallization from ethyl acetate

Sources & evidence

ORD record
ord-a87b06ce1ca84f23a3a85056b315ecb6
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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