Iodine → (2R)-2-Amino-3-(4-fluorophenyl)propan-1-ol

Temperature

0 °C

To the solution of sodium borohydride (0.48 g, 13.1 mmol) in THF (10 mL) was added D-4-fluorophenylalanine (1.0 g, 5.5 mmol). After cooling to 0° C., the solution of iodine (1.4 g, 5.5 mmol) in THF (10 mL) was added dropwisely. The mixture was stirred at reflux for 18 h. after cooling to the room temperature, methanol (7 mL) was added to stop the reaction. After removal of solvent, 20% potassium hydroxide (50 mL) was added. The mixture was stirred for 4 h and extracted with methylene chloride (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-10% methanol in methylene chloride in 30 min afforded (R)-2-(4-fluoro-phenyl)-1-hydroxymethyl-ethylamine (0.73 g, 79%).

1. temperatureat reflux for 18 h.
2. additionwas added
3. customthe reaction
4. customAfter removal of solvent, 20% potassium hydroxide (50 mL)
5. additionwas added
6. stirringThe mixture was stirred for 4 h
7. extractionextracted with methylene chloride (3×50 mL)
8. dry with materialThe combined organic layers were dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-d2e8cb9b3a7d492081781287f9feb2ff

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07326786B2