Cyclopentanol → HCID 54260599, compound

HRID 1154442Notes

Reaction equation

HRID 1154442 reaction equation
[I:1][C:2]1[C:7]2[C:8](=[O:25])[N:9]3[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])([CH3:21])C)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:26]1(O)CCC[CH2:27]1>CCO.CCO.CCO.CCO.[Ti].[F-].[K+]>[I:1][C:2]1[C:7]2[C:8](=[O:25])[N:9]3[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[CH2:22][CH2:27][CH2:26][CH2:21]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7298CyclopentanolHCID 54532449HCID 54532449, compound

Product 1

HCID 54260599HCID 54260599, compound

Reagents, catalysts & solvents 2

HCID 2724286Titanium(IV)ethoxideCatalystHCID 522689Potassium FluorideSolvent

Procedure

3.5 g (7.7 mmol) of tert.butyl (S)-12,12a-dihydro-8-iodo-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylate, 10 g (116 mmol) of cyclopentanol and 0.8 g (3 mmol) of tetraethyl orthotitanate are stirred at 125° overnight, the solution obtained is evaporated and the residue is taken up in chloroform. The solution obtained is 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 a rapid filtration through about 200 g of silica gel while eluting with ethyl acetate and subsequent crystallization from ethyl acetate there is obtained cyclopentyl (S)-12,12a-dihydro-8-iodo-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylate of melting point 184°-185°.

Workup

  1. customthe solution obtained
  2. customis evaporated
  3. customThe solution obtained
  4. filtrationthe resulting emulsion is filtered over siliceous earth
  5. customthe organic phase is separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. filtrationBy a rapid filtration through about 200 g of silica gel
  10. washwhile eluting with ethyl acetate and subsequent crystallization from ethyl acetate

Sources & evidence

ORD record
ord-7e089877318c482f9532ac8f3a69b16a
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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