Cyclopropanemethanol → HCID 54343207, compound

HRID 1154440Notes

Reaction equation

HRID 1154440 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(C)(C)C)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.O[CH2:28][CH:29]1[CH2:31][CH2:30]1>[F-].[K+]>[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][CH2:28][CH:29]3[CH2:31][CH2:30]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 75644CyclopropanemethanolHCID 10718981HCID 10718981, compound

Product 1

HCID 54343207HCID 54343207, compound

Reagents, catalysts & solvents 1

HCID 522689Potassium FluorideSolvent

Procedure

4.65 g (10 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, 24 g (330 mmol) of hydroxymethyl-cyclopropane and 3 g (13 mmol) of tetraethyl crthotitanate are stirred at 115° overnight, the solution is evaporated to dryness 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 through siliceous earth, the organic phase is separated, washed with water, dried over magnesium sulphate and evaporated. By crystallization from ethyl acetate and hexane there is obtained cyclopropylmethyl (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 164°-165°.

Workup

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

Sources & evidence

ORD record
ord-a21fe9e994594467ab05856fc9b42eed
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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