(2-{3-[1-(5-Fluoro-pyridin-2-yl)-vinyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine → (2-{3-[1-(5-Fluoro-pyridin-2-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine

Participants

Reaction Steps

To a solution of (2-{3-[1-(5-fluoro-pyridin-2-yl)-vinyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine (133 mg, 0.407 mmol) in ethanol (7 mL), platinum dioxide (50 mg, 0.2 mmol) was added. Reaction was shaken at 35 psi for 3 hours and at 40 psi for 3 hours under an atmosphere of hydrogen. The reaction mixture was filtered and washed with EtOH. Purification by mass triggered preparative HPLC afforded (2-{3-[1-(5-fluoro-pyridin-2-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine (Compound 7-3). (MH+=329, tR=40.592, Method 2) The enantiomers (2-{3-[(R)-1-(5-fluoro-pyridin-2-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine (Compound 7-4) (MH+=329.0, tR=4.617, Method 2) and (2-{3-[(S)-1-(5-fluoro-pyridin-2-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine (Compound 7-5) (MH+=329.0, tR=4.554, Method 2) were separated using a chiral HPLC OJ-H column, Eluent: Hexanes:EtOH=90:10 with 0.1% DEA.

Provenance & Evidence