(3S)-3-hydroxy-3-phenylpropanenitrile → (1S)-3-amino-1-phenylpropan-1-ol

To a THF solution of (S)-3-phenyl-3-hydroxypropanenitrile was slowly added THF solution of borane dimethyl sulfide complex at room temperature. Methyl sulfide was then distilled from the reaction vessel and the resulting THF solution 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 (S)-3-phenyl-3-hydroxypropylamine.

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

ORD record

ord-6e2ece804d7d4ca8a8ffb642556a2c8b

Source dataset

uspto-grants-2005_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06838581B2