Aluminium lithium hydride → (2RS)-4-amino-2-(3,4-dichlorophenyl)-1-methoxybutan-2-ol

HRID 1022579Notes

Reaction equation

HRID 1022579 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([OH:16])([CH2:13][O:14][CH3:15])[CH2:10][C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:12][CH2:11][CH2:10][C:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)([OH:16])[CH2:13][O:14][CH3:15]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66976168(3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-methoxybutanenitrile

Product 1

HCID 66975521(2RS)-4-amino-2-(3,4-dichlorophenyl)-1-methoxybutan-2-olYield 53.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-methoxybutanenitrile (5.56 g) in THF (100 mL) was added lithium aluminum hydride (812 mg) by small portions at room temperature. The mixture was stirred at room temperature for 10 min, and the reaction mixture was quenched with water. The precipitate was filtered off, and washed with THF. The filtrate was concentrated, 0.1 N aqueous potassium hydroxide solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (NH, eluent; hexane:ethyl acetate (0%-100%)) to give the title compound (3.02 g).

Workup

  1. customthe reaction mixture was quenched with water
  2. filtrationThe precipitate was filtered off
  3. washwashed with THF
  4. concentrationThe filtrate was concentrated
  5. addition0.1 N aqueous potassium hydroxide solution was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated
  10. customThe residue was purified by silica gel column chromatography (NH, eluent; hexane:ethyl acetate (0%-100%))

Sources & evidence

ORD record
ord-5703391a81f4437fadd43624243e7c29
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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