(S)-2-Amino-2-(3-fluorophenyl)ethanol

Used as an intermediate in laboratory research.

(Rs,2S)-N-((tert-butyldimethylsilyloxy)-1-(4-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide (0.280 g, 0.749 mmol) was dissolved in MeOH (10 mL) and then HCl/MeOH (4 M, 2.0 mL) was added. The solution was stirred at room temperature for 3 h. After that, the solvent was removed under vacuum and the residue neutralized with saturated NaHCO₃ (20 mL). The mixture was extracted with CH₂Cl₂/MeOH and the organic phases dried (Na2SO4) and concentrated to obtained (S)-2-Amino-2-(3-fluorophenyl)ethanol.

By coupling an amine group to a carboxyl group, (S)-2-Amino-2-(3-fluorophenyl)ethanol could be employed to synthesize (S)-N-{1-(3-fluorophenyl)-2-hydroxyethyl}-4-{5-methyl-2-(phenylamino)pyrimidin-4-yl}-1H-pyrrole-2-carboxamide..

(S)-2-Amino-2-(3-fluorophenyl)ethanol can be prepared by the amination reaction of 1-Ethenyl-3-fluorobenzene and ammonia water.

[1] Tetrahedron Asymmetry, 2011, vol. 22, # 3, p. 329 - 337