Uses
(S)-(-)-1-(4-Fluorophenyl)ethylamine is used in organic synthesis. It acts as a ligand and form a coordination complex, diacetato-2-O-bis[(S)-1-(4-fluorophenyl)ethylamine-N]palladium(II) by reacting with palladium(II) acetate.
Synthesis
General procedure for the synthesis of (S)-1-(4-fluorophenyl)ethylamine using 4-fluoroacetophenone as starting material: to a vial containing 4-fluoroacetophenone (0.2 mmol, 1.0 eq.), ammonium formate (HCO2NH4, 37.8 mg, 2 mmol, 10.0 eq.), and Pdα-nanocatalyst (Pd°-AmP-MFC, 2.68 mg. 0.002 mmol, 8 wt%) were added to the vial with methanol (0.3 mL) and the reaction mixture was stirred for the time indicated in Table 4. Upon completion of the reaction, the vials were cooled in an ice bath, followed by the addition of methanol (0.367 mL) and a buffer solution (50 mM HEPES, pH 8.2, 6 mL) containing aminotransferase (ATA) and 2-5 equivalents of sodium pyruvate (1 equivalent = 0.2 mmol, 22 mg). The reaction tubes were placed under light-avoiding conditions and left to stand at room temperature for 24 h with gentle shaking on an orbital oscillator. Upon completion of the reaction, the enantiomeric excess (ee) of the product was determined by high performance liquid chromatography (HPLC) analysis (repeated three times for each sample).
References
[1] Patent: WO2016/96905, 2016, A1. Location in patent: Page/Page column 25
[2] Chemistry Letters, 2004, vol. 33, # 11, p. 1424 - 1425
[3] Journal of Organic Chemistry, 2013, vol. 78, # 11, p. 5314 - 5327
[4] Organic Process Research and Development, 2014, vol. 18, # 6, p. 788 - 792
[5] ACS Catalysis, 2016, vol. 6, # 6, p. 3932 - 3940
