2-Amino-1-(4-fluorophenyl)ethan-1-ol → [Rac]-(4-tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-2-hydroxy-ethyl]-amine

0.52 ml of 4-tert-butylbenzaldehyde (3.1 mmol) and 320 mg of [rac]-2-amino-1-(4-fluoro-phenyl)-ethanol (2.06 mmol) were dissolved in 15 ml methanol at rt, and after stirring for 5 min at rt, were refluxed for 2 h. After cooling down to rt, 117 mg (3.1 mmol) of sodium borohydride were added and after stirring for 15 min at rt, the reaction mixture was then refluxed for 2 h. After cooling down to rt, the residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue was stirred with diethylether/heptane, filtered and the solid dried under high vacuo, leading to 410 mg of [rac]-(4-tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-2-hydroxy-ethyl]-amine as a white solid (66%). MS (ISP) 302.2 (M+H)+.

1. temperaturewere refluxed for 2 h
2. temperatureAfter cooling down to rt
3. stirringafter stirring for 15 min at rt
4. temperaturethe reaction mixture was then refluxed for 2 h
5. temperatureAfter cooling down to rt
6. customAfter separation of the organic phase
7. extractionthe aqueous phase was extracted with EtOAc
8. washthe combined organic phases were washed with brine
9. dry with materialdried with magnesium sulfate
10. filtrationfiltered off
11. concentrationconcentrated in vacuo
12. stirringThe residue was stirred with diethylether/heptane
13. filtrationfiltered
14. customthe solid dried under high vacuo

ORD-Eintrag

ord-1a908dc1f5b248aeac627f21184b3903

Quelldatensatz

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07259183B2