Aluminium lithium hydride → HCID 66852447, compound

HRID 1668515Notes

Reaction equation

HRID 1668515 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Si:7]([O:14][CH2:15][C:16]1[N:21]=[C:20]([CH2:22][CH2:23][C:24]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=O)[CH:19]=[CH:18][CH:17]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>C1COCC1>[Si:7]([O:14][CH2:15][C:16]1[N:21]=[C:20]([CH2:22][CH2:23][CH2:24][N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)[CH:19]=[CH:18][CH:17]=1)([C:10]([CH3:13])([CH3:11])[CH3:12])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58105210HCID 58105210, compound

Product 1

HCID 66852447HCID 66852447, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 420 mg of LiAlH4 in 20 mL of THF, the solution of 1.9 g of 3-[6-(t-butyldimethylsilanyl-oxymethyl)pyridin-2-yl]-1-morpholin-4-ylpropan-1-one in 30 mL of THF was added dropwise at ice temperature. After the reaction mixture was stirred at room temperature for 3 hours, the excess LiAlH4 was quenched with water, and the solution was filtrated through Hyflo Super-Cel (Nacalai Tesque) and partitioned. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, the residue was purified by chromatography on silica gel (methylene chloride-ethanol 40:1) to give 760 mg of 4-{3-[6-(t-butyldimethylsilanyloxymethyl)pyridin-2-yl]propyl}morpholine.

Workup

  1. customthe excess LiAlH4 was quenched with water
  2. filtrationthe solution was filtrated through Hyflo Super-Cel (Nacalai Tesque)
  3. custompartitioned
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removing the solvent under reduced pressure
  7. customthe residue was purified by chromatography on silica gel (methylene chloride-ethanol 40:1)

Sources & evidence

ORD record
ord-b45a225d5a674da8a82b0193c3c9bc3d
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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