1-Phenethylamine, (-)- → (S)-3-[2-(4-Fluoro-2-methyl-phenyl)-ethyl]-3-hydroxy-4-methyl-pentanoic Acid

Participants

Reaction Steps

Compound G-16 (enriched—62% (S)-enantiomer/38% (R) enantiomer) (11.1 g, 41.5 mmol) was dissolved in 120 mL EtOAc and treated with (S)-α-methylbenzylamine (6.52 g, 53.79 mmol). The resulting suspension was heated to reflux until all solids dissolved, at which time the solution was allowed to cool to room temperature overnight. The reaction flask was cooled to 0° C. for 1 hour. The resulting solids were filtered off and washed with cold Et2O. HPLC analysis of isolated solid (as the free acid): (AS chiralpak column, 0.8 mL/min., 98% Hexanes/2% IPA/+0.1% Formic acid).

Provenance & Evidence