Aluminium lithium hydride → HCID 178461292, compound

HRID 1913517Notes

Reaction equation

HRID 1913517 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([N:14]2[CH:18]=[C:17]([C:19](OCC)=[O:20])[N:16]=[CH:15]2)[CH2:10][CH2:9]1>O1CCCC1.C(OCC)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>[CH3:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([N:14]2[CH:18]=[C:17]([CH2:19][OH:20])[N:16]=[CH:15]2)[CH2:12][CH2:13]1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178469800HCID 178469800, compound

Product 1

HCID 178461292HCID 178461292, compoundYield 88.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 24436Sodium SulfateSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (92%, 0.31 g) was suspended in tetrahydrofuran (6 mL). The compound (1.50 g) obtained in Step 1 of this Reference Example was dissolved in tetrahydrofuran (6 mL), and this solution was slowly added dropwise to the suspension at 0° C. After stirring at 0° C. for 30 minutes, the reaction solution was diluted with diethyl ether, and saturated aqueous sodium sulfate was added thereto. After stirring at room temperature for 1 hour, the formed inorganic salt was removed by filtration through celite. The filtrate was concentrated under reduced pressure to obtain a crude product. This crude product was washed with a mixed solvent of hexane and ethyl acetate (5:1) to obtain the title compound (1.09 g).

Workup

  1. additionthis solution was slowly added dropwise to the suspension at 0° C
  2. additionwas added
  3. stirringAfter stirring at room temperature for 1 hour
  4. customthe formed inorganic salt was removed by filtration through celite
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto obtain a crude product
  7. washThis crude product was washed with a mixed solvent of hexane and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-3aad4181673b43a7ae80afc2efa3c891
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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