Diisobutylaluminumhydride → HCID 25127948, compound

HRID 2240957Notes

Reaction equation

HRID 2240957 reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH:31]([F:33])[F:32])=[CH:26][CH:25]=4)[C:20](=[O:21])[N:19]([CH3:22])[C:18]([NH2:23])=[N:17]3)[CH:11]=2)[CH2:7]1)C.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[NH2:23][C:18]1[N:19]([CH3:22])[C:20](=[O:21])[C:16]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH:31]([F:33])[F:32])=[CH:28][CH:29]=2)([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([CH:8]3[CH2:9][C:6](=[CH:5][CH2:4][OH:3])[CH2:7]3)[CH:11]=2)[N:17]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 59790314HCID 59790314, compound

Product 1

HCID 25127948HCID 25127948, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(3-{3-[2-Amino-4-(4-difluoromethoxy-phenyl)-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl]-phenyl}-cyclobutylidene)-acetic acid ethyl ester (0.202 g, 0.430 mmol) was dissolved in tetrahydrofuran (THF, 2 mL) and chilled in an ice bath. To this solution was added a 1 M solution of diisobutylaluminum hydride (DIBAL) in THF (11 ml). The reaction was stirred for 1 hour at ambient temperature, and then quenched with crushed ice, followed by addition of sodium chloride and ammonium chloride salts. The crude mixture was extracted with diethyl ether and dried with magnesium sulfate to yield a yellow oil 33 mg (18%); MS (ES) m/z 426.1 [M−H]−.

Workup

  1. temperaturechilled in an ice bath
  2. customquenched with crushed ice
  3. additionfollowed by addition of sodium chloride and ammonium chloride salts
  4. extractionThe crude mixture was extracted with diethyl ether
  5. dry with materialdried with magnesium sulfate

Sources & evidence

ORD record
ord-a4f7a21ca5eb40758e564ff6f831de5c
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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