Cyclopropanemethanol → HCID 53707248, compound

HRID 1154467Notes

Reaction equation

HRID 1154467 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[C:10]3[C@@H:9]3[CH2:22][CH2:23][CH2:24][N:8]3[C:7](=[O:25])[C:6]=2[C:26]=1[Cl:27].O[CH2:29][CH:30]1[CH2:32][CH2:31]1>CCO.CCO.CCO.CCO.[Ti]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([O:17][CH2:29][CH:30]4[CH2:32][CH2:31]4)=[O:16])=[C:10]3[C@@H:9]3[CH2:22][CH2:23][CH2:24][N:8]3[C:7](=[O:25])[C:6]=2[C:26]=1[Cl:27]

Participants

4

Reactant 2

HCID 75644CyclopropanemethanolHCID 57012809HCID 57012809, compound

Product 1

HCID 53707248HCID 53707248, compound

Reagents, catalysts & solvents 1

HCID 2724286Titanium(IV)ethoxideCatalyst

Procedure

A mixture of 4.0 g (7.3 mmol) of tert.butyl (S)-7,8-dichloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate, 10 ml (126 mmol) of hydroxymethyl-cyclopropane and 1 g (3 mmol) of tetraethyl orthotitanate is stirred at 125° overnight, the mixture is evaporated and the residue is taken up in chloroform. The solution is stirred for 0.5 hour with 30 ml of a saturated potassium fluoride solution and the mixture is filtered through siliceous earth. The organic phase is separated, washed with water, dried over magnesium sulphate and evaporated. By crystallization from ethyl acetate there is obtained cyclopropylmethyl (S)-7,8-dichloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 185°-186°.

Workup

  1. customthe mixture is evaporated
  2. stirringThe solution is stirred for 0.5 hour with 30 ml of a saturated potassium fluoride solution
  3. filtrationthe mixture 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

Sources & evidence

ORD record
ord-34d43566e96c424f983809d3b0aa3df1
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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