Hydrochloric Acid → (R)-3-Amino-1-phenyl-propan-1-ol

HRID 1760080Notes

Reaction equation

HRID 1760080 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]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10130035(3R)-3-hydroxy-3-phenylpropanenitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customat room temperature
  2. temperaturethe resulting solution was refluxed for 2.5 h
  3. additionwas added to the reaction mixture
  4. customMethanol and methyl borate were removed by distillation
  5. extractionExtraction of the mixture with dichloromethane,followed
  6. concentrationby concentration

Sources & evidence

ORD record
ord-6fd6b3bd1fc44e6494259b36ac039070
Source dataset
uspto-grants-2005_01
Patent number
US06838581B2

Reaction notes

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