(3R)-3-hydroxy-3-phenylpropanenitrile → (R)-3-Amino-1-phenyl-propan-1-ol

HRID 1760081Notes

Reaction equation

HRID 1760081 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C@H:13]([OH:17])[CH2:14][C:15]#[N:16])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[C:7]1([C@H:13]([OH:17])[CH2:14][CH2:15][NH2:16])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 10130035(3R)-3-hydroxy-3-phenylpropanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 11182697(R)-3-Amino-1-phenyl-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring suspension of lithium aluminum hydride in dry THF at 0° C. was added a solution of (R)-3-phenyl-3-hydroxypropanenitrile in dry THF under nitrogen. The ice bath was removed and then the reaction mixture was refluxed for 2 h. Excess lithium aluminum hydride was destroyed by adding H2O and EtOAc. The white precipitate obtained was filtered and washed with MeOH. The combined filtrate was concentrated to give (R)-3-phenyl-3-hydroxypropylamine.

Workup

  1. customThe ice bath was removed
  2. temperaturethe reaction mixture was refluxed for 2 h
  3. customExcess lithium aluminum hydride was destroyed
  4. additionby adding H2O and EtOAc
  5. customThe white precipitate obtained
  6. filtrationwas filtered
  7. washwashed with MeOH
  8. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-3ffdb403336b4bdb868e4548367bd326
Source dataset
uspto-grants-2005_01
Patent number
US06838581B2

Reaction notes

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