Water → HCID 57248251, compound

HRID 654867Notes

Reaction equation

HRID 654867 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C@:15]([OH:27])([C@@H:22]([CH3:26])[C@@H:23]1[O:25][CH2:24]1)[CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1.O>C(OCC)C>[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C@:15]([OH:27])([C@@H:22]([CH3:26])[C@@H:23]([OH:25])[CH3:24])[CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 57140205HCID 57140205, compound

Product 1

HCID 57248251HCID 57248251, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

84 mg (2.16 mmole) of lithium aluminum hydride were added, under an atmosphere of nitrogen, to a solution of 320 mg (1.08 mmole) of (2R*,3S*,4S*)-2-(2,4-difluoro-phenyl)-4,5-epoxy-3-methyl-1-(1H-1,2,4-triazol-1-yl)-2-pentanol (stereoisomer A) [prepared as described in step (a) above] in 20 ml of diethyl ether, whilst ice-cooling and stirring. Ten minutes later the reaction mixture was heated under reflux, and this was continued for hour. At the end of this time, the mixture was cooled, and 2 ml of water were slowly added; the mixture was then stirred for 10 minutes. The insoluble materials in the reaction mixture were removed by filtration using a Celite filter aid, and then the residue was washed with ethyl acetate. The combined filtrate and washings were dried and freed from the solvent by distillation under reduced pressure. The resulting oily residue was subjected to column chromatography through silica gel, using a 5:5:1 by volume mixture of ethyl acetate, chloroform and hexane as the eluent, to afford 240 mg of the title compound.

Workup

  1. temperaturewhilst ice-cooling
  2. temperatureTen minutes later the reaction mixture was heated
  3. temperatureunder reflux
  4. waitthis was continued for hour
  5. temperatureAt the end of this time, the mixture was cooled
  6. stirringthe mixture was then stirred for 10 minutes
  7. customThe insoluble materials in the reaction mixture were removed by filtration
  8. filtrationfilter aid
  9. washthe residue was washed with ethyl acetate
  10. customThe combined filtrate and washings were dried
  11. distillationfreed from the solvent by distillation under reduced pressure
  12. additionby volume mixture of ethyl acetate, chloroform and hexane as the eluent

Sources & evidence

ORD record
ord-4af58c8015b245ba871ab7ef112fad02
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

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