Benzylamine → (1S)-1-(4-fluorophenyl)-2-(benzylamino)ethanol

Participants

Reaction Conditions

Reaction Steps

Charge a 10 L round bottom flask with (S)-2-(4-fluorophenyl)oxirane (880 g, 6.38 mol) under a nitrogen atmosphere. Add benzylamine (2047 g, 19.13 mol) while the mixture is maintained at 20° C. Heat the mixture to 80° C. and stir it at that temperature for 5 h. Cool to 22° C. and stir for 16 h. Add H2O (3 L) to quench the reaction. Filter and wash the filter cake with water (2×1 L). Slurry the solid obtained with heptane (2 L) and filter to give the title compound (1216 g, 77%). MS (m/z): 246 (M+1); ee value: 99.0% (AD-H 250 mm×4.6 mm×5 μm column using 90:10 hexanes (with 0.02% diethylamine):EtOH at 25° C. with a flow rate of 1.0 mL/min).

Provenance & Evidence