Aluminum(III) Chloride → (2RS)-4-amino-2-(3,4-dichlorophenyl)-1-(4-methoxyphenoxy)butan-2-ol

HRID 1022585Notes

Reaction equation

HRID 1022585 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:11][C:12]1[CH:13]=[C:14]([C:19]([OH:33])([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[CH2:20][C:21]#[N:22])[CH:15]=[CH:16][C:17]=1[Cl:18]>C(OCC)C.C1COCC1>[NH2:22][CH2:21][CH2:20][C:19]([C:14]1[CH:15]=[CH:16][C:17]([Cl:18])=[C:12]([Cl:11])[CH:13]=1)([OH:33])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 66975141(3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-(4-methoxyphenoxy)butanenitrile

Product 1

HCID 66976055(2RS)-4-amino-2-(3,4-dichlorophenyl)-1-(4-methoxyphenoxy)butan-2-olYield 91.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of lithium aluminum hydride (2.53 g) in diethyl ether (50 mL) was added aluminum chloride (2.96 g), and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added dropwise a solution of (3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-(4-methoxyphenoxy)butanenitrile (11.7 g) in THF (50 mL), and the mixture was stirred at 0° C. for 15 min, and then stirred while warming to room temperature for 2 hr. To the reaction mixture was added ice, and the precipitate was filtered off through celite. The filtrate was diluted with water, and the mixture was extracted with ethyl acetate. The obtained extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (10.8 g).

Workup

  1. stirringthe mixture was stirred at 0° C. for 15 min
  2. stirringstirred
  3. temperaturewhile warming to room temperature for 2 hr
  4. additionTo the reaction mixture was added ice
  5. filtrationthe precipitate was filtered off through celite
  6. additionThe filtrate was diluted with water
  7. extractionthe mixture was extracted with ethyl acetate
  8. extractionThe obtained extract
  9. washwas washed with brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1f00b27df1ba482d901399b330f5f5e4
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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