Aluminium lithium hydride → HCID 59408740, compound

HRID 1188125Notes

Reaction equation

HRID 1188125 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1)[C:9]1[S:10][C:11]([C:14](OCC)=[O:15])=[CH:12][N:13]=1>C1COCC1>[CH3:7][N:8]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1)[C:9]1[S:10][C:11]([CH2:14][OH:15])=[CH:12][N:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 594087635-Thiazolecarboxylic acid, 2-[methyl(tetrahydro-2H-pyran-2-yl)amino]-, ethyl ester

Product 1

HCID 59408740HCID 59408740, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

LiAlH4 (425 mg, 11.20 mmol) was added to a solution of ethyl 2-(methyl(tetrahydro-2H-pyran-2-yl)amino)thiazole-5-carboxylate (2.02 g, 7.47 mmol) in THF (20 mL) at 0° C. in small portions. After stirring at 0° C. for 30 min, the reaction was quenched slowly by H2O (1 mL), 5% NaOH (3 mL) and again H2O (5 mL). Then AcOEt was added. The reaction mixture was dried with Na2SO4 and filtered through celite. The filtrate was concentrated and purified by column chromatography (30%-50% AcOEt/PE gradient), yielding (2-(methyl-(tetrahydro-2H-pyran-2-yl)amino)thiazol-5-yl)methanol (1.5 g, 93%) as an oil.

Workup

  1. customthe reaction was quenched slowly by H2O (1 mL), 5% NaOH (3 mL) and again H2O (5 mL)
  2. additionThen AcOEt was added
  3. dry with materialThe reaction mixture was dried with Na2SO4
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated
  6. custompurified by column chromatography (30%-50% AcOEt/PE gradient)

Sources & evidence

ORD record
ord-ed8422639acd4a978076b7bda50a119b
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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