(S)-1-phenylethanaMine (S)-2-((1-(2-(trifluoroMethyl)phenyl)ethoxy)carbonyl)benzoate synthesis

Yield:90.6 % de

Reaction Conditions:

in tetrahydrofuran;n-heptane;toluene at 25 - 34;

Steps:

2

170.0g of the diastereomer salt was added to 510mL of methanol, followed by dissolving it by heating at 60°C, gradual cooling to 5°C, filtering the precipitated crystals, and vacuum drying, thereby obtaining 99.4g of a recrystallized product of the diastereomer salt of (S)-1-(2-trifluoromethylphenyl)ethyl alcohol phthalate half ester-(S)-1-phenylethylamine represented by the above formula. Optical purity of the recrystallized product was 98.9%ee by determination by chiral chromatography. Recovery of the recrystallized product was 61.0%. ¹H-NMR and ¹⁹F-NMR spectrums of the obtained diastereomer salt of (S)-1-(2-trifluoromethylphenyl)ethyl alcohol phthalate half ester-(S)-1-phenylethylamine are shown in the following. ¹H-NMR (standard substance: (CH₃)₄Si, deuterated solvent: CDCl₃), δ ppm: 1.51 (d, 6.8Hz, 3H), 1.61 (d, 6.8Hz, 3H), 3.68 (br, 3H), 4.26 (q, 6.8Hz, 1H), 6.37 (q, 6.8Hz, 1H), 7.24-7.82 (Ar-H, 13H). ¹⁹F-NMR (standard substance: C₆F₆, deuterated solvent: CDCl₃), δ ppm: 103.20 (S, 3F).

References:

EP1935866,2008,A1 Location in patent:Page/Page column 15-16