Water → (r)-2-((4-Methoxybenzyl)amino)propan-1-ol

HRID 1045666Notes

Reaction equation

HRID 1045666 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[NH2:11][C@@H:12]([CH2:14][OH:15])[CH3:13].[BH4-].[Na+].O>CO>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:1][NH:11][C@H:12]([CH3:13])[CH2:14][OH:15])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 312444-MethoxybenzaldehydeHCID 80308(R)-(-)-2-Amino-1-propanolHCID 4311764Sodium borohydride

Product 1

HCID 60073967(r)-2-((4-Methoxybenzyl)amino)propan-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Anisaldehyde (18.1 g, 133 mmol) was added to a solution of D-alaninol (10 g, 133 mmol) in methanol (100 ml) with vigorous stirring and the mixture was stirred for 30 minutes. Sodium borohydride (5.0 g, 132 mmol) was added to the ice-cooled solution and stirred for one hour at room temperature. When the reaction was complete (checked by thin layer chromatography), excess reagent was decomposed by the addition of water. The solution was partitioned between water and chloroform. The organic layer was washed with brine, dried over magnesium sulfate. Removal of the solvent under reduced pressure afforded (2R)-2-(4-Methoxybenzylamino)-propan-1-ol (26 g, 133 mmol, 100%) as white crystals.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. temperaturecooled solution
  3. stirringstirred for one hour at room temperature
  4. customThe solution was partitioned between water and chloroform
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-8e8fa34f97d44b11a16ca3ade3b81ec3
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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