Aluminium lithium hydride → HCID 86722315, compound

HRID 874826Notes

Reaction equation

HRID 874826 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:18])[C:5](=[O:17])[NH:6][C:7]1[CH:16]=[CH:15][C:10]([C:11](OC)=[O:12])=[CH:9][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:1][CH2:2][CH2:3][N:4]([CH3:18])[C:5]([NH:6][C:7]1[CH:16]=[CH:15][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=1)=[O:17]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86722314HCID 86722314, compound

Product 1

HCID 86722315HCID 86722315, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−78° C.) solution of methyl 4-(3-(2-hydroxyethyl)-3-methylureido)benzoate (2.02 g, 8.00 mmol) in THF (80 mL) was added a solution of lithium aluminium hydride (2.0 M solution in THF, 6.0 mL, 12.0 mmol). After 20 minutes the coolant was removed and the reaction mixture stirred at RT for 18 h. The reaction mixture was quenched with water (0.46 mL), 2 M aqueous sodium hydroxide (0.46 mL) and water (3×0.46 mL). The mixture was diluted with ethyl acetate and magnesium sulfate added. The mixture stirred for 1 hour and then filtered. The filtrate was evaporated at reduced pressure and the residue was purified by flash column chromatography eluting with 0 to 100% ethyl acetate/iso-hexane to afford the title compound (1.09 g, 60%).

Workup

  1. customAfter 20 minutes the coolant was removed
  2. customThe reaction mixture was quenched with water (0.46 mL), 2 M aqueous sodium hydroxide (0.46 mL) and water (3×0.46 mL)
  3. additionThe mixture was diluted with ethyl acetate and magnesium sulfate
  4. additionadded
  5. stirringThe mixture stirred for 1 hour
  6. filtrationfiltered
  7. customThe filtrate was evaporated at reduced pressure
  8. customthe residue was purified by flash column chromatography
  9. washeluting with 0 to 100% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-f63695ace3fc476bbd2536de6a0ade36
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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