1-Phenethylamine, (+)- → HCID 15604588, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of racemic 2-{2-[5-fluoro-2-(methyloxy)phenyl]-2-methylpropyl}-2-(trifluoromethyl)oxirane (which may be prepared according to WO04/063163, 600 mg, 2.05 mmol) in anhydrous EtOH (3 mL) was added (R)-(+)-1-phenylethylamine (1.31 mL, 10.3 mmol). The reaction mixture was then stirred and heated at 50° C. under nitrogen overnight and then for 5 days, cooled to room temperature and evaporated in vacuo. The residue was applied to a 70 g silica SPE cartridge and eluted with 0.5% NH3 in toluene. The appropriate fractions were combined and evaporated in vacuo to give a colourless oil (991.4 mg). 710 mg of this oil was separated by chiral HPC on a 2 inch×15 cm Chiralpak AD column eluted with 25% acetonitrile/0.25M ammonium phosphate (pH 4.9) with a flow rate of 70 mL/min to give Intermediate 9 (2S isomer, 230 mg) after 17.5 min and Intermediate 10 (2R isomer, 200 mg) after 24.8 min.

Provenance & Evidence