DL-beta-Phenylalanine → 1-Propanol, 3-amino-3-phenyl-

Temperature

0 °C

To a suspension of 3-amino-3-phenylpropanoic acid (2.0 g, 12.1 mmol) in dry THF (45 mL) cooled to 0° C. under N2 was added portionwise over 20 minutes solid LiAlH4 (920 mg, 24.2 mmol). Stirring was continued at room temperature for 24 h. after which time solid Na2SO4.10H2O was added with stirring until only a heavy white precipitate was present. The organic layer was diluted with ether and filtered through Celite® and the concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL) and extracted with 1N HCl (3×40 mL). The aqueous layers were combined and basified to pH˜12 with 5M NaOH. The aqueous phase was extracted with ethyl acetate (3×50 mL) and the combined organic phases dried (Na2SO4) and concentrated in vacuo to separate the product which was used without further purification (0.9 g, 49%).

1. stirringwith stirring until only a heavy white precipitate
2. filtrationfiltered through Celite®
3. concentrationthe concentrated in vacuo
4. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
5. extractionextracted with 1N HCl (3×40 mL)
6. extractionThe aqueous phase was extracted with ethyl acetate (3×50 mL)
7. dry with materialthe combined organic phases dried (Na2SO4)
8. concentrationconcentrated in vacuo
9. customto separate the product which
10. customwas used without further purification (0.9 g, 49%)

ORD record

ord-1af4c3a2cb1a4287b3e79d0b83c658a2

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084456B2