Hydrochloric Acid → (1R)-3-amino-1-phenylpropan-1-ol
Reaction equation
[C:1]1([C@H:7]([OH:11])[CH2:8][C:9]#[N:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C1COCC1>[C:1]1([C@H:7]([OH:11])[CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a THF solution of (R)-3-phenyl-3-hydroxypropanenitrile was slowly added borane THF complex at room temperature and then the resulting solution was refluxed for 2.5 h. After cooling to room temperature methanolic HCl was added to the reaction mixture. Methanol and methyl borate were removed by distillation and the reaction mixture neutralized with sodium hydroxide (5N). Extraction of the mixture with dichloromethane,followed by concentration provided the crystalline (R)-3-phenyl-3-hydroxypropylamine.
Workup
- customat room temperature
- temperaturethe resulting solution was refluxed for 2.5 h
- additionwas added to the reaction mixture
- customMethanol and methyl borate were removed by distillation
- extractionExtraction of the mixture with dichloromethane,followed
- concentrationby concentration
Sources & evidence
- ORD record
- ord-6fd6b3bd1fc44e6494259b36ac039070
- Source dataset
- uspto-grants-2005_01
- Patent number
- US06838581B2
Reaction notes
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