Water → 3-Amino-2-phenylpropan-1-ol

HRID 2053326Notes

Reaction equation

HRID 2053326 reaction equation
[C:1]1([CH:7]([C:13]#[N:14])[C:8](OCC)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[OH:9][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:13][NH2:14]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 95298Ethyl phenylcyanoacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 112865663-Amino-2-phenylpropan-1-olYield 20%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To the suspension of ethyl phenylcyanoacetate (1.0 g, 5.3 mmol) in anhydrous ether (200 mL) was added lithium aluminum hydride at 0° C. The mixture was stirred at 0° C. for 18 h. After adding water (1 equiv.), 15% sodium hydroxide (1 equiv.) and water (3 equiv.) to the above solution, the precipitation was removed by filtration. The filtrate was concentrate to dry by lyophilization. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-10% methanol in methylene chloride (0.1% NH4OH) in 30 min afforded 3-hydroxy-2-phenyl-propylamine (0.16 g, 20%).

Workup

  1. customthe precipitation
  2. customwas removed by filtration
  3. concentrationThe filtrate was concentrate
  4. customto dry by lyophilization

Sources & evidence

ORD record
ord-62f5e630c1be4fdd950e62c2f81a85e6
Source dataset
uspto-grants-2008_02
Patent number
US07326786B2

Reaction notes

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