Diisobutylaluminumhydride → N-(4-{2-[4-(hydroxymethyl)phenyl]ethyl}thiazol-2-yl)acetamide

HRID 2117873Notes

Reaction equation

HRID 2117873 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16](OC)=[O:17])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.C1(C)C=CC=CC=1>[OH:17][CH2:16][C:15]1[CH:20]=[CH:21][C:12]([CH2:11][CH2:10][C:8]2[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][CH:7]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 21914929HCID 21914929, compound

Product 1

HCID 21914951N-(4-{2-[4-(hydroxymethyl)phenyl]ethyl}thiazol-2-yl)acetamideYield 63%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}benzoate (1.8 g) in dry tetrahydrofuran (36 ml) was added dropwise 1.0 M diisobutylaluminium hydride solution in toluene (20.7 ml) at −78° C. over 15 minutes under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 1.5 hours, and then the reaction was quenched with water (1 ml). The mixture was stirred at room temperature for 30 minutes, dried over anhydrous magnesium sulfate, and filtered through a pad of Celite. The solvent was evaporated in vacuo. The residual solid was washed with ethyl ether to give N-(4-{2-[4-(hydroxymethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (1.03 g) as a colorless solid.

Workup

  1. customthe reaction was quenched with water (1 ml)
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered through a pad of Celite
  5. customThe solvent was evaporated in vacuo
  6. washThe residual solid was washed with ethyl ether

Sources & evidence

ORD record
ord-34edc7f2e3774c8080abe697b4b6f541
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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