Water → HCID 57296556, compound

HRID 654869Notes

Reaction equation

HRID 654869 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])[CH: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 54266318HCID 54266318, compound

Product 1

HCID 57296556HCID 57296556, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

53 mg (1.40 mmole) of lithium aluminum hydride were added, under an atmosphere of nitrogen, to a solution of 207 mg (0.70 mmole) of (2R*,3R*)-2-(2,4-difluorophenyl)-4,5-epoxy-3-methyl-1-(1H-1,2,4-triazol-1-yl)-2-pentanol [about a 3:1 mixture of isomers at the C4 position, prepared as described in Preparation 3] in 4 ml of diethyl ether, whilst ice-cooling and stirring. Ten minutes later the reaction mixture was heated under reflux, and this was continued for 1 hour. At the end of this time, the mixture was cooled, and 1 ml of water was slowly added, after which the mixture was stirred for 10 minutes. The insoluble materials were removed by filtration using a Celite filter aid, after which the residue was washed with ethyl acetate. The combined filtrate and washings were dried over anhydrous sodium sulfate, and the solvent was removed 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 160 mg of the title compound.

Workup

  1. additionabout a 3:1 mixture of isomers at the C4 position
  2. customprepared
  3. temperaturewhilst ice-cooling
  4. temperatureTen minutes later the reaction mixture was heated
  5. temperatureunder reflux
  6. temperatureAt the end of this time, the mixture was cooled
  7. stirringafter which the mixture was stirred for 10 minutes
  8. customThe insoluble materials were removed by filtration
  9. filtrationfilter aid
  10. washafter which the residue was washed with ethyl acetate
  11. dry with materialThe combined filtrate and washings were dried over anhydrous sodium sulfate
  12. customthe solvent was removed by distillation under reduced pressure
  13. additionby volume mixture of ethyl acetate, chloroform and hexane as the eluent

Sources & evidence

ORD record
ord-1b665f2a881b42f985392946a5d0341a
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

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