(3R)-3-hydroxy-3-phenylpropanenitrile → (1R)-3-amino-1-phenylpropan-1-ol
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customThe ice bath was removed
- temperaturethe reaction mixture was refluxed for 2 h
- customExcess lithium aluminum hydride was destroyed
- additionby adding H2O and EtOAc
- customThe white precipitate obtained
- filtrationwas filtered
- washwashed with MeOH
- 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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