Cyclopropanemethanol → HCID 54361250, compound

HRID 1154434Notes

Reaction equation

HRID 1154434 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(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>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][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 107926Bretazenil

Product 1

HCID 54361250HCID 54361250, 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, 31 g (430 mmol) of hydroxymethyl-cyclopropane 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 from ethyl acetate and hexane there is obtained cyclopropylmethyl (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 135°-136°.

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 from ethyl acetate and hexane

Sources & evidence

ORD record
ord-dbc6ecadf9b2401ba401f38b1789b2e8
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

Loading…