1-Azido-3-phenylpropan-2-ol → 1-Amino-3-phenylpropan-2-ol

HRID 33973Notes

Reaction equation

HRID 33973 reaction equation
[N:1]([CH2:4][CH:5]([OH:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+]=[N-].[H][H]>CO.[OH-].[OH-].[Pd+2]>[NH2:1][CH2:4][CH:5]([OH:13])[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 137648321-Azido-3-phenylpropan-2-olHCID 178418361HCID 178418361, compound

Product 1

HCID 37580461-Amino-3-phenylpropan-2-ol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a stirring solution of 1-azido-3-phenyl-propan-2-ol (590 mg, 3.4 mmol) in 20 mL methanol under a nitrogen atmosphere was added 10 mg of Pd(OH)2/C (10%). Hydrogen gas was delivered via balloon. The solution was stirred overnight at room temperature. The catalyst was removed by filtering the solution through a bed of celite, and the filtrate was concentrated to give a clear oil under reduced pressure. M+1=152.

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering the solution through a bed of celite
  3. concentrationthe filtrate was concentrated
  4. customto give a clear oil under reduced pressure

Sources & evidence

ORD record
ord-987ea3f29efc4e5fa71b35482fd86102
Source dataset
uspto-grants-2008_09
Patent number
US07429594B2

Reaction notes

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