Cyclohexanol → HCID 54468936, compound

HRID 1154479Notes

Reaction equation

HRID 1154479 reaction equation
[NH2:1][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]>[NH2:1][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[CH2:22][CH2:32][CH2:27][CH2:28][CH2:20]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7966CyclohexanolHCID 53851583HCID 53851583, compound

Product 1

HCID 54468936HCID 54468936, compound

Reagents, catalysts & solvents 1

HCID 2724286Titanium(IV)ethoxideCatalyst

Procedure

A mixture of 10.0 g (28.2 mmol) of tert.butyl (S)-8-amino-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate, 2.6 g (11.1 mmol) of a tetraethyl orthotitanate and 60 ml of cyclohexanol is stirred at 130° for 24 hours, a small amount of solvent being distilled off three times in vacuo. The mixture is subsequently evaporated in vacuo, the residue is taken up in 60 ml of chloroform, the chloroform solution is treated with water, stirred for a further 1 hour, filtered over siliceous earth and then the organic phase is separated. The organic phase is dried over magnesium sulphate and evaporated. The residue is chromatographed on silica gel while eluting with ethyl acetate and subsequently recrystallized from ethyl acetate. There is obtained cyclohexyl (S)-8-amino-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 211°-212°.

Workup

  1. distillationa small amount of solvent being distilled off three times in vacuo
  2. customThe mixture is subsequently evaporated in vacuo
  3. additionthe chloroform solution is treated with water
  4. stirringstirred for a further 1 hour
  5. filtrationfiltered over siliceous earth
  6. customthe organic phase is separated
  7. dry with materialThe organic phase is dried over magnesium sulphate
  8. customevaporated
  9. customThe residue is chromatographed on silica gel
  10. washwhile eluting with ethyl acetate
  11. customsubsequently recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5d80d0ef072a45599949846ab3c0778f
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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